Cesium carbonate → 4-(2-Chloro-pyridin-3-ylamino)-N-cyclopropylmethyl-2-trifluoromethyl-benzenesulfonamide

HRID 1485007Notes

Reaction equation

HRID 1485007 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+].[Cl:72][C:73]1[C:78]([NH2:79])=[CH:77][CH:76]=[CH:75][N:74]=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:72][C:73]1[C:78]([NH:79][C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]3[CH2:15][CH2:14]3)(=[O:10])=[O:9])=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=2)=[CH:77][CH:76]=[CH:75][N:74]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 805282-Chloro-3-pyridylamineHCID 634876Binap, (A+-)-HCID 249483674-bromo-N-(cyclopropylmethyl)-2-(trifluoromethyl)benzenesulfonamide

Product 1

HCID 249467084-(2-Chloro-pyridin-3-ylamino)-N-cyclopropylmethyl-2-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-Bromo-N-cyclopropylmethyl-2-trifluoromethyl-benzenesulfonamide (150 mg), Pd(OAc)2 (9.5 mg), BINAP (26 mg), cesium carbonate (164 mg) and 2-Chloro-pyridin-3-ylamine (108 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 (1:1). 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 25 mg, 15%.

Workup

  1. washThe reaction mixture was eluted through a silica bed with Toluene
  2. customthe solvent of the PE:EtOAc fraction was removed under reduced pressure
  3. customThe crude product was purified by Combiflash (linear gradient PE-THF)

Sources & evidence

ORD record
ord-19647fe899654b119e212658bcacbbd1
Source dataset
uspto-grants-2016_08
Patent number
US09422235B2

Reaction notes

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