Dimethylformamide → HCID 71267520, compound

HRID 1505773Notes

Reaction equation

HRID 1505773 reaction equation
Br[C:2]1[C:3]([CH3:36])=[C:4]([NH:8][C:9]([C:11]2[C:19]3[N:18]=[C:17]([CH2:20][O:21][CH3:22])[NH:16][C:15]=3[CH:14]=[C:13]([NH:23][C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])=[O:25])[CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:37][N:38](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:37]([C:2]1[C:3]([CH3:36])=[C:4]([NH:8][C:9]([C:11]2[C:19]3[N:18]=[C:17]([CH2:20][O:21][CH3:22])[NH:16][C:15]=3[CH:14]=[C:13]([NH:23][C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:34])([F:33])[F:35])=[O:25])[CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1)#[N:38]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 71267507HCID 71267507, compound

Product 1

HCID 71267520HCID 71267520, compound

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
100 °C

Procedure

To a solution of N-(3-bromo-2-methylphenyl)-2-(methoxymethyl)-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (Example 38) (85 mg) in DMF (0.5 mL), was added zinc cyanide (60% content, 60 mg). After degassing, to the mixture was added tetrakis(triphenylphosphine) palladium (88 mg), and it was stirred at 100° C. for 24 hours. To the reaction mixture was added ice water, and it was extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified on preparative thin-layer chromatography to obtain the titled compound (14 mg) as colorless powder.

Workup

  1. customAfter degassing, to the mixture
  2. additionwas added tetrakis(triphenylphosphine) palladium (88 mg), and it
  3. additionTo the reaction mixture was added ice water, and it
  4. extractionwas extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed sequentially with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified on preparative thin-layer chromatography

Sources & evidence

ORD record
ord-0093d03f63bc43fd811abe5ddb573891
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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