Sodium hydride → {(2-Bromo-4-cyano-phenyl)-[6-oxo-2-(3-trifluoromethyl-phenylamino)-cyclohex-1-enyl]-methyl}-carbamic acid tert-butyl ester

HRID 59652Notes

Reaction equation

HRID 59652 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH:11]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[C:21]([O:25][C:26](=[O:47])[NH:27][CH:28](S(C1C=CC=CC=1)(=O)=O)[C:29]1[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][C:30]=1[Br:37])([CH3:24])([CH3:23])[CH3:22]>CC1CCCO1>[C:21]([O:25][C:26](=[O:47])[NH:27][CH:28]([C:29]1[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][C:30]=1[Br:37])[C:11]1[C:12](=[O:16])[CH2:13][CH2:14][CH2:15][C:10]=1[NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:17])([F:18])[F:1])[CH:4]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27486303-{[3-(Trifluoromethyl)phenyl]amino}cyclohex-2-en-1-one2×HCID 118691238Tert-butyl N-[(Benzenesulfonyl)(2-bromo-4-cyanophenyl)methyl]carbamate2×

Product 1

HCID 118692170{(2-Bromo-4-cyano-phenyl)-[6-oxo-2-(3-trifluoromethyl-phenylamino)-cyclohex-1-enyl]-methyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent

Procedure

3-(3-Trifluoromethyl-phenylamino)-cyclohex-2-enone (INTERMEDIATE 3, 10.7 g, 42 mmol) is suspended in 2-methyl-tetrahydrofurane (150 mL) and sodium hydride (60% in mineral oil) (1.76 g, 43.9 mmol) is added in portions. The mixture is stirred at room temperature for 20 min and [benzenesulfonyl-(2-bromo-4-cyano-phenyl)-methyl]-carbamic acid tert-butyl ester (INTERMEDIATE 19, 16.5 g, 36.6 mmol) is added. The mixture is stirred for 1 h at room temperature. The organic phase is washed with water, dried over MgSO4 and concentrated. The product is precipitated from cyclohexane. Yield: 20.6 g. ESI mass spectrum: [M+H]+=564 (bromine isotope pattern); Retention time HPLC: 0.81 min (X012_S02).

Workup

  1. stirringThe mixture is stirred for 1 h at room temperature
  2. washThe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe product is precipitated from cyclohexane
  6. custom0.81 min (X012_S02)

Sources & evidence

ORD record
ord-bfcc20558529444c9f62818932824d14
Source dataset
uspto-grants-2016_09
Patent number
US09440930B2

Reaction notes

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