Aniline → N-Cyclopropylmethyl-4-phenylamino-2-trifluoromethyl-benzenesulfonamide

HRID 1485001Notes

Reaction equation

HRID 1485001 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.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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+]>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:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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 6115AnilineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 249483674-bromo-N-(cyclopropylmethyl)-2-(trifluoromethyl)benzenesulfonamide

Product 1

HCID 24948368N-Cyclopropylmethyl-4-phenylamino-2-trifluoromethyl-benzenesulfonamideYield 20%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-bromo-N-cyclopropylmethyl-2-trifluoromethylbenzenesulfonamide (183 mg, 0.51 mmol), aniline (93 mg, 1.0 mmol), Pd(OAc)2 (11 mg, 0.05 mmol), BINAP (33 mg, 0.05 mmol) and cesium carbonate (246 mg, 0.75 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 20%

Workup

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

Sources & evidence

ORD record
ord-a320e677cf7e445183f34a48f3aad4d9
Source dataset
uspto-grants-2016_08
Patent number
US09422235B2

Reaction notes

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