5-[4-(Trifluoromethyl)phenyl]-1,3-cyclohexanedione → 3-(3-Carbomethoxy-2-bromoanilino)-5-(4-trifluoromethylphenyl)-cyclohex-2-en-1-one

HRID 51334Notes

Reaction equation

HRID 51334 reaction equation
[Br:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:13][C:14]([F:30])([F:29])[C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][C:25](=O)[CH2:24][C:23](=[O:28])[CH2:22]2)=[CH:17][CH:16]=1>>[C:4]([C:3]1[C:2]([Br:1])=[C:11]([CH:10]=[CH:9][CH:8]=1)[NH:12][C:25]1[CH2:26][CH:21]([C:18]2[CH:19]=[CH:20][C:15]([C:14]([F:30])([F:29])[F:13])=[CH:16][CH:17]=2)[CH2:22][C:23](=[O:28])[CH:24]=1)([O:6][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 5991275-[4-(Trifluoromethyl)phenyl]-1,3-cyclohexanedioneHCID 13574117Methyl 3-amino-2-bromobenzoate

Product 1

HCID 227395153-(3-Carbomethoxy-2-bromoanilino)-5-(4-trifluoromethylphenyl)-cyclohex-2-en-1-oneYield 74%

Conditions

Temperature
150 °C

Procedure

A mixture of methyl 2-bromo-3-aminobenzoate (10.2 g, 44.3 mM) and 5-(4-trifluoromethylphenyl)-1,3-cyclohexanedione (1.77 g, 6.93 mM) was heated at 150° C. under a stream of nitrogen for 20 minutes. The resultant solid was triturated with 4:1 EtOAc/Et2O to afford 2.18 g (74%) of 3-(3-carbomethoxy-2-bromoanilino)-5-(4-trifluoromethylphenyl)-cyclohex-2-en-1-one. 1H NMR (DMSO-d6) δ8.9 (s, 1H), 7.75-7.5 (m, 7H), 3.9 (s, 3H), 3.5 (m, 1H), 2.9 (dd, J=14 and 9 Hz, 1H), 2.7 (dd, J14 and 4 Hz, 1H), 2.55 (dd, J=14 and 9 Hz, 1H), 2.35 (dd, J=14 and 4 Hz, 1H). MS (ES) m/e 368, 370.

Workup

  1. customThe resultant solid was triturated with 4:1 EtOAc/Et2O

Sources & evidence

ORD record
ord-3e67e647b8484c8ab6984a8d18e3bad3
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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