Methanol → HCID 58087116, compound

HRID 1964997Notes

Reaction equation

HRID 1964997 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.CO.[F:13][CH:14]([F:28])[O:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([O:24][CH:25]([F:27])[F:26])[CH:23]=1)[CH:19]=[O:20].[OH-].[K+]>O>[F:13][CH:14]([F:28])[O:15][C:16]1[CH:17]=[C:18]([CH:19]([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:20])[CH:21]=[C:22]([O:24][CH:25]([F:26])[F:27])[CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 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 962WaterSolvent

Procedure

To 5-bromo-7-azaindole (67, 86.4 mg, 0.000438 mol) 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 art 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-1476653847da43e382702179f8ae6515
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

Loading…