Water → HCID 58087116, compound

HRID 1261151Notes

Reaction equation

HRID 1261151 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.[F:11][CH:12]([F:26])[O:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([O:22][CH:23]([F:25])[F:24])[CH:21]=1)[CH:17]=[O:18].[OH-].[K+].O>CO>[F:11][CH:12]([F:26])[O:13][C:14]1[CH:15]=[C:16]([CH:17]([C:5]2[C:4]3[C:8](=[N:9][CH:10]=[C:2]([Br:1])[CH:3]=3)[NH:7][CH:6]=2)[OH:18])[CH:19]=[C:20]([O:22][CH:23]([F:24])[F:25])[CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 58086499HCID 58086499, compound

Product 1

HCID 58087116HCID 58087116, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5-bromo-7-azaindole (67, 86.4 mg, 0.000438 mol) in methanol (10.0 mL) were added 3,5-bis-difluoromethoxy-benzaldehyde (529, 110.0 mg, 0.46 mmol) and potassium hydroxide (200.0 mg, 3.6 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight. 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 20% ethyl acetate in hexane to give the compound as a white solid (530, 70 mg, 35%). MS (ESI) [M+H+]+=435.1, 437.1.

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 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-05fbcd362eb847b3acaf4fc7c83fe732
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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