Potassium Carbonate → 2-(6-ethynyl-1H-benzoimidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 79725Notes

Reaction equation

HRID 79725 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[C:19]1[NH:23][C:22]2[CH:24]=[C:25]([C:28]#[C:29][Si](C)(C)C)[CH:26]=[CH:27][C:21]=2[N:20]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>CO>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[C:19]1[NH:23][C:22]2[CH:24]=[C:25]([C:28]#[CH:29])[CH:26]=[CH:27][C:21]=2[N:20]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 666201682-(6-trimethylsilanylethynyl-1H-benzoimidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 722403932-(6-ethynyl-1H-benzoimidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (144 mg) was added to 2-(6-trimethylsilanylethynyl-1H-benzoimidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (200 mg, 0.52 mmol) in 6 ml methanol. The reaction was stirred at room temperature for 2 hours. The reaction mixture was concentrated and purified by flash column chromatography (silica gel, 20 to 100% ethyl acetate/hexane) to give 2-(6-ethynyl-1H-benzoimidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (121 mg, yield 75%). LCMS-ESI−: calc'd for C18H21N3O2: 311.38. Found: 311.8 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash column chromatography (silica gel, 20 to 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3cc2f8cbe97242ea8e4a88a0084207a3
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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