Water → (5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-[6-chloro-2-fluoro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-methanol

HRID 1964996Notes

Reaction equation

HRID 1964996 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[Cl:11][C:12]1[C:17]([CH:18]=[O:19])=[C:16]([F:20])[C:15]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:14][CH:13]=1.[OH-].[K+].O>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:18]([C:17]3[C:12]([Cl:11])=[CH:13][CH:14]=[C:15]([O:21][CH2:22][C:23]([F:25])([F:26])[F:24])[C:16]=3[F:20])[OH:19])=[CH:6][NH:7][C:8]2=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 595068296-Chloro-2-fluoro-3-(2,2,2-trifluoro-ethoxy)-benzaldehyde

Product 1

HCID 59506814(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-[6-chloro-2-fluoro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5-bromo-7-azaindole (67, 291 mg, 1.48 mmol) in methanol mL) were added 6-Chloro-2-fluoro-3-(2,2,2-trifluoro-ethoxy)-benzaldehyde (523, 400.0 mg, 1.6 mmol) and potassium hydroxide (1.49 g, 26.6 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature for 48 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 25% ethyl acetate in hexane to give the compound (524, 300 mg, 42%). MS (ESI) [M+H+]+=453.1, 455.1.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 25% ethyl acetate in hexane
  7. customto give the compound (524, 300 mg, 42%)

Sources & evidence

ORD record
ord-96172d9b7ee44d2ea9ccb2ec06fe3450
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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