Sodium borohydride → HCID 178424041, compound

HRID 2174017Notes

Reaction equation

HRID 2174017 reaction equation
[CH:1]([C:3]1[C:11]2[C:10]([C:12]([C:14]3[NH:18][C:17]4[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:16]=4[N:15]=3)=[O:13])=[C:9]([CH3:25])[CH:8]=[C:7]([CH3:26])[C:6]=2[NH:5][CH:4]=1)=O.[BH4-].[Na+]>CO.CCOC(C)=O.FC(F)(F)CO>[CH3:1][C:3]1[C:11]2[C:10]([C:12]([C:14]3[NH:18][C:17]4[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:16]=4[N:15]=3)=[O:13])=[C:9]([CH3:25])[CH:8]=[C:7]([CH3:26])[C:6]=2[NH:5][CH:4]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178424044HCID 178424044, compound

Product 1

HCID 178424041HCID 178424041, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 86701615HCID 86701615, compoundSolvent

Procedure

To a solution of 2-(3-formyl-5,7-dimethyl-1H-indole-4-carbonyl)-1H-benzo[d]imidazole-5-carbonitrile (20 mg, 0.058 mmol) in MeOH (2 mL) was added NaBH4 (11.05 mg, 0.292 mmol), and then the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with EtOAc/2,2,2-trifluoroethanol (c.a. 9/1). The organic phase was successively washed by H2O and brine, dried over Na2SO4, and filtered. Concentration of the filtrate gave the title compound, which was used in the next reaction without any further purification. MS (ESI+) m/z 329.1 (M+H).

Workup

  1. washThe organic phase was successively washed by H2O and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered

Sources & evidence

ORD record
ord-4cc394611e624a32876748c5a917c28f
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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