1-(Bromomethyl)-4-(trifluoromethyl)benzene → HCID 24801326, compound

HRID 883157Notes

Reaction equation

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

Participants

Reactant 2

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzene

HCID 24799233HCID 24799233, compound

Product 1

HCID 24801326HCID 24801326, compoundYield 41%

Procedure

Following the procedure as described in Example 2, making variation as required to use N-(3-fluorobenzyl)-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide in place of N-(4-fluorobenzyl)-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamide to react with 1-(bromomethyl)-4-(trifluoromethyl)benzene, the title compound was obtained as a white solid in 41% yield: mp 177-178° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.52 (d, J=8.1 Hz, 2H), 7.30-7.27 (m, 3H), 7.10-6.92 (m, 3H), 6.11 (t, J=5.6 Hz, 1H), 4.56 (d, J=5.6 Hz, 2H), 4.33-4.21 (m, 1H), 4.00-3.88 (m, 1H), 3.53-3.56 (m, 1H), 2.94-2.73 (m, 2H), 2.62 (s, 3H), 2.11-1.95 (m, 1H), 1.94-1.75 (m, 2H), 1.62-1.43 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 171.7, 162.9, 162.7, 156.9, 152.4, 143.2, 140.6, 130.3, 129.6, 128.9, 125.9, 125.5, 125.4, 123.3, 122.4, 119.3, 114.7, 114.5, 48.0, 43.9, 43.3, 37.3, 24.9, 21.3, 17.4; MS (ES+) m/z 506.3 (M+1).

Sources & evidence

ORD record: ord-c9d2bdfd191647d48a18aa8ba3d9b45b
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236835B2

Reaction notes

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