4-Fluorobenzyl bromide → HCID 68492837, compound

HRID 2381858Notes

Reaction equation

C(NC(C1SC(C2N=CNN=2)=CC=1C)=O)C1C=CC=CC=1.[CH3:22][C:23]1[CH:27]=[C:26]([C:28]2[N:32]=[CH:31][NH:30][N:29]=2)[S:25][C:24]=1[C:33]([NH:35][CH2:36][C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)=[O:34].[F:43][C:44]1[CH:51]=[CH:50][C:47]([CH2:48]Br)=[CH:46][CH:45]=1>>[F:43][C:44]1[CH:51]=[CH:50][C:47]([CH2:48][N:30]2[CH:31]=[N:32][C:28]([C:26]3[S:25][C:24]([C:33]([NH:35][CH2:36][C:37]4[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=4)=[O:34])=[C:23]([CH3:22])[CH:27]=3)=[N:29]2)=[CH:46][CH:45]=1

Participants

Reactant 3

HCID 680214-Fluorobenzyl bromide

HCID 178423431HCID 178423431, compound

HCID 178423432HCID 178423432, compound

Product 1

HCID 68492837HCID 68492837, compoundYield 24%

Procedure

Following the procedure as described in Example 23, making variations as necessary to replace N-benzyl-3-methyl-5-(1H-1,2,4-triazol-3-yl)thiophene-2-carboxamide with 3-methyl-N-(pyridin-3-ylmethyl)-5-(1H-1,2,4-triazol-3-yl)thiophene-2-carboxamide to react with 4-fluorobenzyl bromide, the title compound was obtained as an off-white solid in 24% yield: mp 154-155° C.; 1H NMR (300 MHz, CDCl3) δ 8.60 (s, 1H), 8.54 (s, 1H), 7.99 (s, 1H), 7.71 (d, J=7.4 Hz, 1H), 7.45 (s, 1H), 7.33-7.24 (m, 3H), 7.11-7.02 (m, 2H), 6.27 (br s, 1H), 5.30 (s, 2H), 4.62 (d, J=5.6 Hz, 2H), 2.52 (s, 3H); MS (ES+) m/z 408.2 (M+1).

Sources & evidence

ORD record: ord-32d216cd390c4c30a74d401c30fca15a
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258160B2

Reaction notes

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