Cesium carbonate → n-Cyclopropylmethyl-4-[(6,6-dimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-amino]-2-trifluoromethyl-benzenesulfonamide

HRID 1485004Notes

Reaction equation

HRID 1485004 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.CC1(C)[C@H]2C[C@@H]1CC[C@H]2C[NH2:29].C1C=CC(P([C:44]2[C:53]([C:54]3[C:63](P(C4C=CC=CC=4)C4C=CC=CC=4)=[CH:62][CH:61]=[C:60]4[C:55]=3C=CC=[CH:59]4)=[C:52]3C(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:29][CH2:59][CH:60]3[CH2:55][CH:54]4[CH2:63][CH:62]([C:53]4([CH3:52])[CH3:44])[CH2:61]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 634876Binap, (A+-)-HCID 11194443Myrtanylamine, cis-(-)-HCID 249483674-bromo-N-(cyclopropylmethyl)-2-(trifluoromethyl)benzenesulfonamide

Product 1

HCID 68522976n-Cyclopropylmethyl-4-[(6,6-dimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-amino]-2-trifluoromethyl-benzenesulfonamideYield 42%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Mixture of 4-bromo-N-cyclopropylmethyl-2-trifluoromethylbenzenesulfonamide (200 mg, 0.55 mmol), (−)-cis-myrtanylamine (153 mg, 1.0 mmol), Pd(OAc)2 (26 mg, 0.1 mmol), BINAP (62 mg, 0.1 mmol) and cesium carbonate (401 mg, 1.26 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 42%

Workup

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

Sources & evidence

ORD record
ord-300ce48f50344046b6aaade3c4420672
Source dataset
uspto-grants-2016_08
Patent number
US09422235B2

Reaction notes

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