1-(Bromomethyl)-4-(trifluoromethoxy)benzene → HCID 24801666, compound

HRID 883146Notes

Reaction equation

HRID 883146 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.[F:14][C:15]1[CH:36]=[CH:35][C:18]([CH2:19][NH:20][C:21]([C:23]2[S:27][C:26]([N:28]3[CH2:32][CH2:31][CH2:30][C:29]3=[O:33])=[N:25][C:24]=2[CH3:34])=[O:22])=[CH:17][CH:16]=1>>[F:14][C:15]1[CH:36]=[CH:35][C:18]([CH2:19][NH:20][C:21]([C:23]2[S:27][C:26]([N:28]3[CH2:32][CH2:31][CH:30]([CH2:2][C:3]4[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=4)[C:29]3=[O:33])=[N:25][C:24]=2[CH3:34])=[O:22])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 16954475HCID 16954475, compound

Product 1

HCID 24801666HCID 24801666, compoundYield 26%

Procedure

Following the procedure as described in Example 2, making variation as required to use 1-(bromomethyl)-4-(trifluoromethoxy)benzene in place of 1-(bromomethyl)-4-(trifluoromethyl)benzene to react with N-(4-fluorobenzyl)-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamide, the title compound was obtained as a white solid in 26% yield: mp 165-166° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.34-7.16 (m, 4H), 7.12 (d, J=8.6 Hz, 2H), 7.01 (t, J=8.6 Hz, 2H), 6.02 (t, J=5.6 Hz, 1H), 4.52 (d, J=5.6 Hz, 2H), 4.09-4.02 (m, 1H), 3.93-3.79 (m, 1H), 3.29-3.20 (m, 1H), 3.05-2.95 (m, 1H), 2.85-2.75 (m, 1H), 2.60 (s, 3H), 2.35-2.19 (m, 1H), 1.99-1.81 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 174.6, 162.3, 155.4, 152.8, 148.1, 136.9, 133.7, 131.6, 130.3, 129.6, 121.2, 118.6, 115.7, 45.9, 44.3, 43.4, 35.7, 24.3, 17.2; MS (ES+) m/z 508.3 (M+1).

Sources & evidence

ORD record
ord-a719864dfe4a4faf9637cd8bbfb66c42
Source dataset
uspto-grants-2012_08
Patent number
US08236835B2

Reaction notes

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