Tetrahydrofuran → HCID 86643170, compound

Participants

Reaction Steps

1-[4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-3-(3-trifluoromethyl-4-vinylphenyl)urea (300 mg, 0.68 mmol) was dissolved in a solution mixture of THF (100 mL) and water (50 mL), and an osmium tetraoxide aqueous solution (0.1 M, 300 μL) and sodium periodide (590 mg, 2.76 mmol) were added thereto. The resulting mixture was stirred at room temperature for 17 hours. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine and concentrated under reduced pressure to give a crude product of 1-[4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-3-(3-trifluoromethyl-4-formylphenyl)urea (229 mg, 76%). Then, this crude formyl compound (59.4 mg, 0.14 mmol) was dissolved in methanol (3 mL), and sodium borohydride (15.5 mg, 0.41 mmol) was added thereto. The resulting mixture was stirred at room temperature for 2 hours. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine and concentrated under reduced pressure to give a crude product of 1-[4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-3-(3-trifluoromethyl-4-hydroxymethylphenyl)urea (50.9 mg, 85%).

Provenance & Evidence