Bromomethyl 2-methoxyphenyl ketone → HCID 66939344, compound

HRID 1255196Notes

Reaction equation

HRID 1255196 reaction equation
[NH2:1][C:2]([N:4]1[C:8](O)([C:9]([F:12])([F:11])[F:10])[CH:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[N:5]1)=[S:3].Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])=O>C(O)C>[CH3:30][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:21]1[N:1]=[C:2]([N:4]2[C:8]([C:9]([F:12])([F:11])[F:10])=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[N:5]2)[S:3][CH:20]=1

Participants

4

Reactant 2

HCID 123440Bromomethyl 2-methoxyphenyl ketoneHCID 12113245HCID 12113245, compound

Product 1

HCID 66939344HCID 66939344, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 1-(aminocarbonothioyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-4-carboxylate (470 mg, 1.65 mmol, prepared according to J. Comb. Chem. 2002, 4, 23-32) and 2-bromo-2′-methoxyacetophenone (377 mg, 1.65 mmol) in ethanol (8 mL) was heated at 80° C. After 1 h, the mixture was allowed to cool to ambient temperature, then was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 55% EtOAc in hexanes) provided the title compound as an off-white solid: LCMS m/z 398.5 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 8.26 (dd, J=7.6, 1.6 Hz, 1H), 8.13 (s, 1H), 8.03 (s, 1H), 7.37 (ddd, J=8.9, 6.5, 1.8 Hz, 1H), 7.12-7.01 (m, 2H), 4.42 (q, J=7.0 Hz, 2H), 4.02 (s, 3H), 1.42 (tr=7.0 Hz, 3H).

Workup

  1. concentrationwas concentrated in vacuo
  2. customPurification by flash chromatography on silica gel (0 to 55% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a8ea1808551e4b5f953ad675fdd3bc89
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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