Potassium trimethylsilanolate → N-(6-(2-fluoro-4-iodophenylamino)-7-fluoro-2,3-dimethyl-2H-indazol-5-yl)cyclopropanesulfonamide
Reaction equation
[CH:1]1([S:4]([N:7]2[C:11]3=[CH:12][C:13]4[C:17]([C:18]([F:19])=[C:10]3[N:9]([C:22]3[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=3[F:29])C2=O)=[N:16][N:15]([CH3:20])[C:14]=4[CH3:21])(=[O:6])=[O:5])[CH2:3][CH2:2]1.C[Si](C)(C)[O-].[K+]>C1COCC1>[F:29][C:23]1[CH:24]=[C:25]([I:28])[CH:26]=[CH:27][C:22]=1[NH:9][C:10]1[C:11]([NH:7][S:4]([CH:1]2[CH2:3][CH2:2]2)(=[O:5])=[O:6])=[CH:12][C:13]2[C:17]([C:18]=1[F:19])=[N:16][N:15]([CH3:20])[C:14]=2[CH3:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-cyclopropanesulfonyl-8-fluoro-7-(2-fluoro-4-iodophenyl)-2,3-dimethyl-2,7-dihydro-5H-imidazo[4,5-f]indazol-6-one (24 mg, 0.044 mmol) in THF (3 ml) was added potassium trimethylsilanolate (11 mg, 0.088 mmol). The reaction was stirred at room temperature for 5 h, quenched with saturated aqueous NH4Cl solution (5 ml), and extracted with EtOAc (2×10 ml). The combined organic solution was washed with brine (15 ml), dried over MgSO4, and concentrated. Silica gel chromatography (EtOAc:Hexanes=50:50) yielded 19 mg (83%) of the title compound. m/z=517 [M−1]−. 1H NMR (DMSO-d6, 400 MHz): δ 0.78 (m, 4H), 2.48 (m, 1H), 2.68 (s, 3H), 4.13 (s, 3H), 6.38 (m, 1H), 7.32 (d, J=8 Hz, 1H), 7.41 (s, 1H), 7.59 (m, 2H), 9.23 (s, 1H).
Workup
- customquenched with saturated aqueous NH4Cl solution (5 ml)
- extractionextracted with EtOAc (2×10 ml)
- washThe combined organic solution was washed with brine (15 ml)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d0269ecc6f8d4793a5ac4cc3e3447377
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063049B2
Reaction notes
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