4-Fluorobenzyl bromide → HCID 24801502, compound

HRID 883156Notes

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]([F:33])=[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:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:15]2=[O:20])=[N:11][C:10]=1[CH3:21])=[O:8]

Participants

Reactant 2

HCID 680214-Fluorobenzyl bromide

HCID 24799233HCID 24799233, compound

Product 1

HCID 24801502HCID 24801502, compoundYield 46%

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-fluorobenzene in place of 1-(bromomethyl)-4-(trifluoromethyl)benzene, the title compound was obtained as a white solid in 46% yield: mp 173-175° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.31-7.24 (m, 1H), 7.15-6.88 (m, 7H), 6.12 (t, J=5.6 Hz, 1H), 4.55 (d, J=5.6 Hz, 2H), 4.29-4.21 (m, 1H), 3.98-3.86 (m, 1H), 3.40-3.27 (m, 1H), 2.86-2.69 (m, 2H), 2.62 (s, 3H), 2.08-1.95 (m, 1H), 1.93-1.73 (m, 2H), 1.61-1.44 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 171.9, 162.9, 162.6, 161.6, 156.9, 152.4, 140.6, 134.5, 130.5, 130.2, 123.2, 119.1, 115.3, 114.6, 114.4, 47.9, 44.1, 43.4, 36.6, 24.8, 21.2, 17.3; MS (ES+) m/z 456.3 (M+1).

Sources & evidence

ORD record: ord-6902f33392454e0a939d8d6e1298d691
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236835B2

Reaction notes

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