3-Fluorobenzyl bromide → HCID 24801156, compound

HRID 883151Notes

Reaction equation

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

Participants

Reactant 2

HCID 680073-Fluorobenzyl bromide

HCID 24799232N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 24801156HCID 24801156, compoundYield 89%

Procedure

Following the procedure as described in Example 2, making variation as required to use N-benzyl-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)-3-fluorobenzene in place of 1-(bromomethyl)-4-(trifluoromethyl)benzene, the title compound was obtained as a white solid in 89% yield: mp 170-171° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.39-7.17 (m, 6H), 6.99-6.89 (m, 3H), 6.01 (t, J=5.5 Hz, 1H), 4.57 (d, J=5.5 Hz, 2H), 4.33-4.21 (m, 1H), 3.99-3.89 (m, 1H), 3.45-3.36 (m, 1H), 3.86-3.27 (m, 2H), 2.63 (s, 3H), 2.10-1.96 (m, 1H), 1.94-1.73 (m, 2H), 1.61-1.43 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 171.8, 162.9, 162.6, 156.9, 152.1, 141.6, 137.9, 130.1, 128.8, 127.9, 127.7, 124.9, 119.5, 114.9, 114.6, 113.6, 48.0, 44.0, 37.3, 24.9, 21.3, 17.4; MS (ES+) m/z 438.2 (M+1).

Sources & evidence

ORD record: ord-a2b37e81f3ba48c1ace08cf5c2b5d580
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236835B2

Reaction notes

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