Methanol → HCID 68432623, compound

HRID 1397852Notes

Reaction equation

HRID 1397852 reaction equation
[CH2:1]([O:8][C:9](=[O:21])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([CH:18]=[O:19])[C:12]=1[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:22]1[C:26]2=[N:27][CH:28]=[C:29]([C:31]#[N:32])[CH:30]=[C:25]2[CH:24]=[CH:23]1.CO.[OH-].[K+]>O>[CH2:1]([O:8][C:9](=[O:21])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([CH:18]([C:24]2[C:25]3[C:26](=[N:27][CH:28]=[C:29]([C:31]#[N:32])[CH:30]=3)[NH:22][CH:23]=2)[OH:19])[C:12]=1[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 117883551H-Pyrrolo[2,3-b]pyridine-5-carbonitrileHCID 58086235Benzyl (2,4-difluoro-3-formylphenyl)carbamate

Product 1

HCID 68432623HCID 68432623, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a reaction vessel, (2,4-difluoro-3-formyl-phenyl)-carbamic acid benzyl ester (25, 10.00 g, 34.3 mmol), 1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (13, 4.91 g, 34.3 mmol), 50.00 mL of anhydrous methanol, and potassium hydroxide (2.77 g, 49.4 mmol) were added under nitrogen and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into 500 mL of water and extracted with 3×500 mL of ethyl acetate. The organic layers were combined and dried over magnesium sulfate, filtered, and the filtrate concentrated under vacuum. The resulting residue was purified using silica gel column chromatography to provide the desired compounds (26, 4.62 g, 31%).

Workup

  1. extractionextracted with 3×500 mL of ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting residue was purified

Sources & evidence

ORD record
ord-a18fbcc2f2934cc79f0904bd433fcea3
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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