Furo[2,3-c]pyridine-5-methanol (9CI)

C14 (770 mg, 3.48 mmol) is dissolved in 10 mL MeOH. 2N NaOH (3 mL, 6 mmol) is added, and the reaction is stirred for 1.5 h at rt. C6 (770 mg, 3.48 mmol) is dissolved in 10 mL MEOH. 2N NAOH (3 mL, 6 mmol) is added, and the reaction is stirred for 1.5 h at rt. The solution is concentrated in vacuo to a residue. Water (20 mL) is added to the residue and extracted with 4 x 10 mL CH2C12. The combined organic layer is dried (K2CO3), filtered, and then concentrated in vacuo to afford furo [2, 3-c] PYRIDIN-5-YL methanol (2 AS A WHITE SOLID (90percent yield). Analysis calculated for CSH7NO2 : C, 64.42 ; H, 4.73 ; N, 9.39. Found: C, 64.60 ; H, 4.56 ; N, 9.44.C4 (32.0 g, 174 mmol) is combined with zinc powder (34.2 g, 523 mmol) in absolute EtOH (900 mL), using an overhead stirrer. The mixture is heated to 70°C, HC1 (87.2 mL, 1.05 mol) is added slowly drop-wise, and the mixture is heated to reflux for 1 h. The mixture is cooled slightly, filtered to remove the metallic zinc and concentrated to near-dryness. The yellow oil is diluted with H20 (150 mL) and EtOAc (950 mL) and is treated slowly drop-wise with 20percent Na2C03 (310 mL) as the mixture is warmed to reflux. The vigorously stirred (using overhead stirrer) mixture is refluxed for 1 h, cooled slightly and the organics removed via cannula under reduced pressure. Additional EtOAc (600 mL) is added, the mixture is heated to reflux for 1 h, cooled slightly and the organics removed as above. More EtOAc (600 mL) is added, the mixture is stirred at rt overnight then heated to reflux for 1 h, cooled slightly and most of the organics removed as above. The remaining mixture is filtered through celite, rinsed with EtOAc until no additional product elutes, and the layers separated. The aqueous layer is further extracted with EtOAc (2 X 400 mL). The combined organics are dried (MGS04) and concentrated to a dark yellow solid (23.6 g). The crude material is chromatographed over 900 g slurry-packed silica gel, eluting with 60percent EtOAc/hexane (3 L), 70percent EtOAc/hexane (2 L), and finally 100percent EtOAc. The appropriate fractions are combined and concentrated in vacuo to'afford C7 (19.5 g, 75percent) as a white solid. Anal. Calcd for CgH7NO2 : C, 64.42 ; H, 4.73 ; N, 9. 39 ; Found: C, 64.60 ; H, 4.56 ; N, 9.44.a-8) (d) (d) (d) Furo[2, 3-c]pyridin-5-ylmethanol; A solution of furo[2, 3-clpyridin-5-ylmethyl acetate (1.15 g) in 1 , 4-dioxane(30 ml) and water (10 ml) was treated with 2M sodium hydroxide (12 ml) then stirred at ambient temperature for 18h. The mixture was then partitioned between (d) Furo[2, 3-c]pyridin-5-ylmethanol; A solution of furo[2, 3-c]pyridin-5-ylmethyl acetate (1.15 g) in 1, 4-dioxane (30ml) and water (10ml) was treated with 2M sodium hydroxide (12ml) then stirred at ambient temperature for 18h. The mixture was then partitioned between ethyl acetate and water. The organic fractions were separated and dried then evaporated to dryness. This gave an oil (0.63g, 70percent). MS (+ve ion electrospray) m/z 150 (MH+).(d) Furo [2, 3 -c]pyridin-5 -ylmethanol; A solution of furo[2, 3-c]pyridin-5-ylmethyl acetate (1.15 g) in 1, 4-dioxane (30 ml) and water (10 ml) was treated with 2M sodium hydroxide (12 ml) then stirred at ambient temperature for 18hrs. The mixture was then partitioned between ethyl acetate and water. The organics were separated and dried then evaporated to dryness. This gave an oil (0.63 g, 70percent). MS (+ve ion electrospray) m/z 150 (MH+).(c) Furo[2, 3-clpyridin-5-ylmethyl acetate; {5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate, trifluoroacetate) (10 g, 22 mmol) was dissolved in pyridine (200 ml) and treated with copper(l) iodide (5.2 g, 27 mmol) then heated under reflux for 18hrs. The mixture was allowed to cool, evaporated to dryness and the residue partitioned between ethyl acetate and water. This mixture was filtered through kieselguhr to remove copper residues. The organic layer was separated from the filtrate, dried and chromatographed on silica gel, eluting with a gradient of 10 - 60percent ethyl acetate in 40-60C14 (770 mg, 3.48 mmol) is dissolved in 10 mL MeOH. 2N NaOH (3 mL, 6 mmol) is added, and the reaction is stirred for 1.5 h at rt. C6 (770 mg, 3.48 mmol) is dissolved in 10 mL MEOH. 2N NAOH (3 mL, 6 mmol) is added, and the reaction is stirred for 1.5 h at rt. The solution is concentrated in vacuo to a residue. Water (20 mL) is added to the residue and extracted with 4 x 10 mL CH2C12. The combined organic layer is dried (K2CO3), filtered, and then concentrated in vacuo to afford furo [2, 3-c] PYRIDIN-5-YL methanol (2 AS A WHITE SOLID (90percent yield). Analysis calculated for CSH7NO2 : C, 64.42 ; H, 4.73 ; N, 9.39. Found: C, 64.60 ; H, 4.56 ; N, 9.44.C4 (32.0 g, 174 mmol) is combined with zinc powder (34.2 g, 523 mmol) in absolute EtOH (900 mL), using an overhead stirrer. The mixture is heated to 70°C, HC1 (87.2 mL, 1.05 mol) is added slowly drop-wise, and the mixture is heated to reflux for 1 h. The mixture is cooled slightly, filtered to remove the metallic zinc and concentrated to near-dryness. The yellow oil is diluted with H20 (150 mL) and EtOAc (950 mL) and is treated slowly drop-wise with 20percent Na2C03 (310 mL) as the mixture is warmed to reflux. The vigorously stirred (using overhead stirrer) mixture is refluxed for 1 h, cooled slightly and the organics removed via cannula under reduced pressure. Additional EtOAc (600 mL) is added, the mixture is heated to reflux for 1 h, cooled slightly and the organics removed as above. More EtOAc (600 mL) is added, the mixture is stirred at rt overnight then heated to reflux for 1 h, cooled slightly and most of the organics removed as above. The remaining mixture is filtered through celite, rinsed with EtOAc until no additional product elutes, and the layers separated. The aqueous layer is further extracted with EtOAc (2 X 400 mL). The combined organics are dried (MGS04) and concentrated to a dark yellow solid (23.6 g). The crude material is chromatographed over 900 g slurry-packed silica gel, eluting with 60percent EtOAc/hexane (3 L), 70percent EtOAc/hexane (2 L), and finally 100percent EtOAc. The appropriate fractions are combined and concentrated in vacuo to'afford C7 (19.5 g, 75percent) as a white solid. Anal. Calcd for CgH7NO2 : C, 64.42 ; H, 4.73 ; N, 9. 39 ; Found: C, 64.60 ; H, 4.56 ; N, 9.44.a-8) (d) (d) (d) Furo[2, 3-c]pyridin-5-ylmethanol; A solution of furo[2, 3-clpyridin-5-ylmethyl acetate (1.15 g) in 1 , 4-dioxane(30 ml) and water (10 ml) was treated with 2M sodium hydroxide (12 ml) then stirred at ambient temperature for 18h. The mixture was then partitioned between (d) Furo[2, 3-c]pyridin-5-ylmethanol; A solution of furo[2, 3-c]pyridin-5-ylmethyl acetate (1.15 g) in 1, 4-dioxane (30ml) and water (10ml) was treated with 2M sodium hydroxide (12ml) then stirred at ambient temperature for 18h. The mixture was then partitioned between ethyl acetate and water. The organic fractions were separated and dried then evaporated to dryness. This gave an oil (0.63g, 70percent). MS (+ve ion electrospray) m/z 150 (MH+).(d) Furo [2, 3 -c]pyridin-5 -ylmethanol; A solution of furo[2, 3-c]pyridin-5-ylmethyl acetate (1.15 g) in 1, 4-dioxane (30 ml) and water (10 ml) was treated with 2M sodium hydroxide (12 ml) then stirred at ambient temperature for 18hrs. The mixture was then partitioned between ethyl acetate and water. The organics were separated and dried then evaporated to dryness. This gave an oil (0.63 g, 70percent). MS (+ve ion electrospray) m/z 150 (MH+).(c) Furo[2, 3-clpyridin-5-ylmethyl acetate; {5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate, trifluoroacetate) (10 g, 22 mmol) was dissolved in pyridine (200 ml) and treated with copper(l) iodide (5.2 g, 27 mmol) then heated under reflux for 18hrs. The mixture was allowed to cool, evaporated to dryness and the residue partitioned between ethyl acetate and water. This mixture was filtered through kieselguhr to remove copper residues. The organic layer was separated from the filtrate, dried and chromatographed on silica gel, eluting with a gradient of 10 - 60percent ethyl acetate in 40-60

Molecular Weight:149.15
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:149.047678466
Monoisotopic Mass:149.047678466
Topological Polar Surface Area:46.3
Heavy Atom Count:11
Complexity:140
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes