Cyclohexylamine → HCID 24947994, compound

HRID 1485003Notes

Reaction equation

HRID 1485003 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][O:14]2)(=[O:10])=[O:9])=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1.[CH:22]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]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:22]1([NH:28][C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]3[CH2:17][CH2:16][CH2:15][O:14]3)(=[O:10])=[O:9])=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 7965CyclohexylamineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 68490910HCID 68490910, compound

Product 1

HCID 24947994HCID 24947994, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Mixture of 4-bromo-N-(tetrahydrofuran-2-ylmethyl)-2-trifluoromethylbenzenesulfonamide (200 mg, 0.51 mmol), cyclohexylamine (193 mg, 1.94 mmol), Pd(OAc)2 (22 mg, 0.10 mmol), BINAP (70 mg, 0.11 mmol) and cesium carbonate (340 mg, 1.01 mmol) in 15 ml toluene was relaxed for 6 hours. Toluene was evaporated in vacuum and crude oil was purified twice by Combiflash (PE-THF). Yield 29%

Workup

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

Sources & evidence

ORD record
ord-b9f5cc73bdde45eebdfa8ab3784d0041
Source dataset
uspto-grants-2016_08
Patent number
US09422235B2

Reaction notes

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