Sodium Bicarbonate → 4-Chloro-1-ethyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1H-pyrazole-5-carboxamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH2:10][CH3:11])[C:6]=1[C:7](Cl)=[O:8].[C:12]1([S:18]([N:21]2[C:29]3[CH:28]=[C:27]([Sn:30]([CH3:33])([CH3:32])[CH3:31])[CH:26]=[C:25]([NH2:34])[C:24]=3[CH:23]=[N:22]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH2:10][CH3:11])[C:6]=1[C:7]([NH:34][C:25]1[CH:26]=[C:27]([Sn:30]([CH3:33])([CH3:32])[CH3:31])[CH:28]=[C:29]2[C:24]=1[CH:23]=[N:22][N:21]2[S:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:20])=[O:19])=[O:8]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
4-Chloro-1-ethyl-1H-pyrazole-5-carbonyl chloride (122 mg) in DCM (5 ml) was added over 5 min to 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (250 mg) in DCM (10 ml) and pyridine (0.05 ml). The reaction was stirred at room temperature for 1.5 h. Saturated sodium bicarbonate (aq) (20 ml) was added and the reaction stirred vigorously before the DCM was passed through a hydrophobic frit and evaporated to dryness. The residue was passed through a silica cartridge, preconditioned with cyclohexane. The silica cartridge was washed with cyclohexane:diethyl ether (1:1, v/v), then diethyl ether. The product containing ether fraction was evaporated to dryness to give title compound, 303 mg.
Workup
- customevaporated to dryness
- washThe silica cartridge was washed with cyclohexane:diethyl ether (1:1
- additionThe product containing ether fraction
- customwas evaporated to dryness
Sources & evidence
- ORD record
- ord-fb6a58974129415e97f9f22e8e12aa62
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658635B2
Reaction notes
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