Tetrabutylammonium Fluoride → 1-(4-Fluoro-phenyl)-1H-indazole-4-carboxylic acid (6-ethynyl-pyridin-3-ylmethyl)-amide
Reaction equation
C[Si]([C:5]#[C:6][C:7]1[N:12]=[CH:11][C:10]([CH2:13][NH:14][C:15]([C:17]2[C:18]3[CH:19]=[N:20][N:21]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:22]=3[CH:23]=[CH:24][CH:25]=2)=[O:16])=[CH:9][CH:8]=1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)C>[C:6]([C:7]1[N:12]=[CH:11][C:10]([CH2:13][NH:14][C:15]([C:17]2[C:18]3[CH:19]=[N:20][N:21]([C:26]4[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=4)[C:22]=3[CH:23]=[CH:24][CH:25]=2)=[O:16])=[CH:9][CH:8]=1)#[CH:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
1-(4-Fluoro-phenyl)-1H-indazole-4-carboxylic acid (6-trimethylsilanylethynyl-pyridin-3-ylmethyl)-amide (70.0 mg, 0.158 mmol) was dissolved in THF (1.0 mL) and treated with a 1 M solution of TBAF in THF (0.16 mL, 0.16 mmol) at room temperature. The solution was stirred for 2 hours and then diluted with diethyl ether (10 mL) and quenched with water (10 mL). The aqueous layers were extracted with diethyl ether (3×5 mL). The combined organic layers were washed with brine (10 mL), dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography eluting with a gradient of 0-70% ethyl acetate in hexanes to afford the title compound as a white solid.
Workup
- customquenched with water (10 mL)
- extractionThe aqueous layers were extracted with diethyl ether (3×5 mL)
- washThe combined organic layers were washed with brine (10 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe crude product was purified by silica gel chromatography
- washeluting with a gradient of 0-70% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-c5d463bc2f004efa8865a8ee618cdc73
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008327B2
Reaction notes
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