1-(Bromomethyl)-4-(trifluoromethoxy)benzene → HCID 67490680, compound

HRID 2408160Notes

Reaction equation

HRID 2408160 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:11]([C:15]2[CH:29]=[CH:28][C:18]([C:19]([NH:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[O:20])=[CH:17][CH:16]=2)[CH2:12][CH2:13][CH3:14])[CH2:9][OH:10])=[CH:4][CH:3]=1.Br[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:41])[F:40])=[CH:34][CH:33]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:11]([C:15]2[CH:16]=[CH:17][C:18]([C:19]([NH:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[O:20])=[CH:28][CH:29]=2)[CH2:12][CH2:13][CH3:14])[CH2:9][O:10][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][C:39]([F:40])([F:41])[F:42])=[CH:34][CH:33]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 58561004HCID 58561004, compound

Product 1

HCID 67490680HCID 67490680, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The major diastereomer of methyl N-(4-{1-[1-(4-chlorophenyl)-2-hydroxyethyl]butyl}benzoyl)-β-alaninate (EXAMPLE 86, Step C, 80 mg, 0.19 mmol), 1-(bromomethyl)-4-(trifluoromethoxy)benzene (97 mg, 0.38 mmol) and Ag2O (87 mg, 0.38 mmol) in DCM (20 mL) was refluxed overnight. After cooling to room temperature, the mixture was filtered, then the filtrate was concentrated. The resulting residue was purified by PTLC to afford the title compound. 1H NMR (300 MHz, CDCl3) δ 7.71 (d, J=8 Hz, 2H); 7.22-7.31 (m, 6H); 7.05-7.12 (m, 4H); 6.90 (t, J=5.4 Hz, 1H); 4.10-4.24 (m, 2H); 332-3.77 (m, 5H); 3.22-3.29 (m, 2H); 2.94-2.98 (m, 2H); 2.67 (t, J=53 Hz, 2H); 1.32-1.44 (m, 2H); 0.88-0.94 (m, 2H); 0.65 (1, J=7.2 Hz, 3H). MS (M+H)+ 592.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified by PTLC

Sources & evidence

ORD record
ord-8ca1503aff884663a27c094dc41d0893
Source dataset
uspto-grants-2014_08
Patent number
US08809579B2

Reaction notes

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