Carbon Dioxide → HCID 57731486, compound

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:22]=[CH:21][N:20]([S:23]([C:26]4[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=4)(=[O:25])=[O:24])[N:19]=3)[CH:16]=2)[N:11]([S:33]([C:36]2[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH:10]=1.C([Li])CCC.[C:48](=[O:50])=[O:49]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:22]=[C:21]([C:48]([OH:50])=[O:49])[N:20]([S:23]([C:26]4[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=4)(=[O:24])=[O:25])[N:19]=3)[CH:16]=2)[N:11]([S:33]([C:36]2[CH:37]=[CH:38][C:39]([CH3:42])=[CH:40][CH:41]=2)(=[O:35])=[O:34])[CH:10]=1

Participants

Procedure

To a cooled solution (−78° C.) of 3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-5-[1-(toluene-4-sulfonyl)-1H-pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine (458 mg, 0.765 mmol) in dry tetrahydrofuran (7 mL) was added 2.5 M n-butyl lithium (n-BuLi) (336 μL. 0.842 mmol) over 15 min. After 2 h at −78° C., a stream of carbon dioxide gas was added to the mixture for 5 min. The reaction was allowed to warm to room temperature. After stirring 3 h, the reaction was quenched by the addition of saturated ammonium chloride and extracted into ethyl acetate. The organic layer was dried over sodium sulfate and purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane to afford 5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-(toluene-4-sulfonyl)-2H-pyrazole-3-carboxylic acid (114 mg, 23%). MS: m/z 643 (M+H+).