Carbon Dioxide → HCID 57731486, compound

HRID 2234711Notes

Reaction equation

HRID 2234711 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

5

Reactant 3

HCID 280Carbon DioxideHCID 57731423HCID 57731423, compoundHCID 178418339Butyllithium

Product 1

HCID 57731486HCID 57731486, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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+).

Workup

  1. customthe reaction was quenched by the addition of saturated ammonium chloride
  2. extractionextracted into ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. custompurified by flash chromatography on silica gel using a gradient of methanol in dichloromethane

Sources & evidence

ORD record
ord-bc085dbfda3147248c9cee9fec83e832
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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