Cesium carbonate → N-Cyclopropylmethyl-4-(3,5-dimethoxy-phenylamino)-2-trifluoromethyl-benzenesulfonamide

HRID 1484999Notes

Reaction equation

HRID 1484999 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.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:26]=[C:27]([O:29][CH3:30])[CH:28]=1)[NH2:25].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+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:13]1([CH2:12][NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:25][C:24]3[CH:26]=[C:27]([O:29][CH3:30])[CH:28]=[C:22]([O:21][CH3:20])[CH:23]=3)=[CH:3][C:4]=2[C:16]([F:19])([F:18])[F:17])(=[O:10])=[O:9])[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 663013,5-DimethoxyanilineHCID 634876Binap, (A+-)-HCID 249483674-bromo-N-(cyclopropylmethyl)-2-(trifluoromethyl)benzenesulfonamide

Product 1

HCID 24825776N-Cyclopropylmethyl-4-(3,5-dimethoxy-phenylamino)-2-trifluoromethyl-benzenesulfonamideYield 48%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Mixture of 4-bromo-N-cyclopropylmethyl-2-trifluoromethylbenzenesulfonamide (295 mg, 0.82 mmol), 3,5-dimethoxyaniline (142 mg, 0.92 mmol), Pd(OAc)2 (26 mg, 0.11 mmol), BINAP (70 mg, 0.11 mmol) and cesium carbonate (395 mg, 1.21 mmol) in 15 ml toluene was relaxed for 6 hours. Toluene was evaporated in vacuum and crude oil was purified by Combiflash (PE-THF). Yield 48%

Workup

  1. customToluene was evaporated in vacuum
  2. customcrude oil was purified by Combiflash (PE-THF)

Sources & evidence

ORD record
ord-a1c540510fa54e86bce9371c93df1a1e
Source dataset
uspto-grants-2016_08
Patent number
US09422235B2

Reaction notes

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