Cesium carbonate → 4-(1-Acetyl-2,3-dihydro-1H-indol-6-ylamino)-N-cyclopropylmethyl-2-trifluoromethyl-benzenesulfonamide
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]2[CH2:15][CH2:14]2)(=[O:10])=[O:9])=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:72][C:73]1[CH:81]=[C:80]2[C:76]([CH2:77][CH2:78][N:79]2[C:82](=[O:84])[CH3:83])=[CH:75][CH:74]=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:82]([N:79]1[C:80]2[C:76](=[CH:75][CH:74]=[C:73]([NH:72][C:2]3[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]4[CH2:15][CH2:14]4)(=[O:10])=[O:9])=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=3)[CH:81]=2)[CH2:77][CH2:78]1)(=[O:84])[CH3:83]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 4-Bromo-N-cyclopropylmethyl-2-trifluoromethyl-benzenesulfonamide (51 mg), Pd(OAc)2 (3.2 mg), BINAP (14 mg), cesium carbonate (55 mg) and 1-(6-Amino-2,3-dihydro-indol-1-yl)-ethanone (50 mg) in 15 ml toluene was relaxed for 12 hours. The reaction mixture was eluted through a silica bed with Toluene and then with PE:EtOAc (70:30). The toluene fraction was discarded and the solvent of the PE:EtOAc fraction was removed under reduced pressure. The crude product was purified by Combiflash (linear gradient PE-THF). Yield 32 mg, 49%.
Workup
- washThe reaction mixture was eluted through a silica bed with Toluene
- customthe solvent of the PE:EtOAc fraction was removed under reduced pressure
- customThe crude product was purified by Combiflash (linear gradient PE-THF)
Sources & evidence
- ORD record
- ord-8f51e8c669a848b9b331306e20f012b0
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422235B2
Reaction notes
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