Water → HCID 58087116, compound

HRID 1098511Notes

Reaction equation

HRID 1098511 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-66ccad4ad39d4e9caea4e5fcfcbfaf0f
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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