1-BENZOFURAN-5-AMINE

Step 1d. Intermediate 11: 12-oxa-5-thia-3-azatricyclo[7.3.0.0{2, 6}]dodeca-1, 3, 6, 8, 10-pentaen-4-amine To a solution of Benzofuran-5-amine (10 mg, 0.08 mmol) and triphosgene (7.5 mg, 0.02 mmol) were dissolved in 2 ml DCM and the solution was cooled to 0C. Triethylamine (21 mI, 0.15 mmol) was added and the solution was stirred at 0 C for 1 h. A solution of 3-methyl-4- phenoxy-aniline (16.5 mg, 0.08 mmol) and trimethylamine (21 mI, 0.15 mmol) in DCM (0.25 ml) was added. The reaction mixture was allowed to reach RT and the reaction was left to stir overnight. The reaction was quenched with 0.5 ml of H2O. NH4CI (aq.sat) and DCM were added and the water phase was extracted further with DCM (x3). The solid present in the combined organic phases was filtered off. The solution was dried over MgSCU and concentrated at reduced pressure to yield 0.026 g (96% yield) of the title compound that was used without further purification in the next step. MS (ESI+) m/z 359 (M+H)+Take a reaction tube, add 50 mg of sodium azide, 48.6 mg of 1-(5-benzofuranyl)ethanol, and 300 uL of trifluoroacetic acid.150 uL of methanesulfonic acid and 1.0 mL of n-hexane were stirred at 40 C for 12 hours.After the reaction was completed, 10 mL of a sodium hydroxide solution was added to quench the reaction, and the mixture was extracted three times with ethyl acetate.Column chromatography gave 21.9 mg of N-(3-carbonyl-2, 3-dihydrobenzofuran-5-yl)acetamide (0.66 g, 3.46 mmol) was dissolved in ethanol (30 ml), 5% palladium carbon (183 mg), hydrogen atmosphere Stir at room temperature overnight and filter off palladium on carbon.After directly adding 3M of dilute hydrochloric acid (30 ml), and heating to reflux for 6h, the solvent was evaporated under reduced pressure, and recrystallized to give a solid (0.42 g) (yield of about 91.3%).

Molecular Weight:133.15
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:133.052763847
Monoisotopic Mass:133.052763847
Topological Polar Surface Area:39.2
Heavy Atom Count:10
Complexity:126
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes