1H-Pyrrolo[2,3-b]pyridin-5-ol

Light yellow solid

To a 50 ml reaction flask at room temperature, the compound of formula II (4.08 g, 11.5 mmol) was added, Copper acetylacetonate (0.15g, 0.575mmol), ΒΗΜΡO (0.15g, 0 · 575mmol), lithium hydroxide monohydrate (2 · 42g, 57.5mmol), 18ml of DMSO, 4.5ml of water, stirring was turned on, replaced with nitrogen, and the temperature was raised to an internal temperature of 100 °C. Temperature reaction for 6 hours. Control raw material reaction is over, stop heating, cool to room temperature (20-30 °C), add water 100ml, adjust PH to 6 with 2N dilute hydrochloric acid, precipitation of solids, suction filtration, aqueous phase with ethyl acetate 50ml * 3 Extraction, combining the organic phases, washing once with water and saturated aqueous sodium chloride solution, drying over anhydrous sodium sulfate, and concentrating the solvent to obtain the compound of formula III. Yield: 1.2 g, yield: 78.5percent.To a 50 ml suffocating tank at room temperature, the compound of Formula IV (4 g, 13.5 mmol), copper iodide (0.128 g, 0.675 mmol), DMEDA (0.06 g, 0.675 mmol), potassium phosphate (2. 86 g, 13 · 5 mmol), water 40 ml, stirring was started, the gas in the stifling tank was replaced with nitrogen, and the temperature was raised to an internal temperature of 160 °C, and the temperature was maintained for 19 hours. The control of the raw material reaction is over, the heating is stopped, the temperature is lowered to room temperature (20-30 °C), the pH is adjusted to 6 with 2N dilute hydrochloric acid, the aqueous phase is extracted with ethyl acetate 50 ml*3, and the organic phases are combined, respectively with water and The solution was washed once with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and the solvent was concentrated to give the compound of formula III. Yield: 1.2 g, yield: 66.2percent.A solution of 5-methoxy-7-azaindole (75 g) and dichloromethane (1500 mL) to was cooled to 0-5°C. Boron tribromide (253 g) was added and the reaction mass was warmed to 27°C and stirred for 4 hours. After cooling to 0-5°C, the reaction mass was quenc hed with methanol (225 mL). The reaction mass was stirred for 1 hour at 27°C.The organic layer was th en concentrated under vacuum at 45°C. Ethyl acetate was added and the reaction mixture was stirred for 2 hours at room temperature before filtering. The obtained solid was washed with ethyl acetate (75 mL) then added to water (450 mL). The pH of the reaction mixture was adjusted to 7-8 using 10percent aqueous sodium bicarbonate solution and then cooled to 0-5°C. The solution was filtered and the solid was washed with deionized water (75 mL). The solid was dried the solid under vacuum oven at 50°C for 4 hou rs. (50 g, Yield: 0.66 w/w).The above 7-azaindole-5-doceteol borate, 220 mL of tetrahydrofuran, 220 mL of 2 M sodium hydroxide solution and 17.5 g of sodium perborate tetrahydrate at room temperature for 2 h (TLC monitoring of 7-azaindole-5-doceteol borate) was complete, the organic phase was separated and the aqueous phase was washed with 10 percent Hydrochloric acid to adjust the pH to 3-4, precipitation of white solid, suction filtration, 100mL water, 50 vacuum drying overnight to obtain 5.8g in white, the yield of 78percent. HPLC purity: 99.2percent.The mixture of methyl 2-fluoro-4- (1, 4-dioxaspiro [4.5] decan-8-yl) benzoate (2.6 g, 8.83 mmol) and 1H-pyrrolo [2, 3-b] pyridin-5-ol (1.42 g, 10.60 mmol) and Cs 2CO 3 in DMF (100 mL) was heated to 100C and stirred overnight. After cooled to room temperature, the reaction mixture was concentrated in vacuum and purified by chromatography column on silica (eluent: EA/PE = 1/5) to give the product (1.16 g, 32.20%) as a yellow solid. MS (ESI, m/e) [M+1] + 409.1

Molecular Weight:134.14
XLogP3:1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:134.048012819
Monoisotopic Mass:134.048012819
Topological Polar Surface Area:48.9
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes