4-Chloro-2-fluorobenzyl bromide → HCID 24951495, compound

HRID 1879184Notes

Reaction equation

HRID 1879184 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[S:15][C:14]([C:16]3[NH:17][N:18]=[CH:19][CH:20]=3)=[N:13][C:12]=2[CH3:21])=[O:10])[CH:2]=1.Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[F:31]>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[S:15][C:14]([C:16]3[CH:20]=[CH:19][N:18]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=4[F:31])[N:17]=3)=[N:13][C:12]=2[CH3:21])=[O:10])[CH:2]=1

Participants

3

Reactant 2

HCID 27365514-Chloro-2-fluorobenzyl bromideHCID 866455594-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide

Product 1

HCID 24951495HCID 24951495, compoundYield 51%

Procedure

The title compound was prepared from 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide and 1-bromomethyl-4-chloro-2-fluoro-benzene as described in Example 49 and isolated as a white solid (0.075 g; 51% yield). 1H NMR (400 MHz, CDCl3) δ 8.61 (s, 1H), 8.56-8.58 (m, 1H), 7.71 (d, J=8 Hz, 1H), 7.46 (d, J=4 Hz, 1H), 7.26-7.31 (m, 1H), 7.10-7.17 (m, 3H), 6.85 (s, 1H), 6.07-6.15 (m, 1H), 5.36 (s, 2H), 4.62 (d, J=8 Hz, 2H), 2.75 (s, 3H). MS (M+H)+=442.1; Rt=1.35 min; HRMS (M+H)+=442.09.

Workup

  1. customisolated as a white solid (0.075 g; 51% yield)

Sources & evidence

ORD record
ord-bf34d88e6da44c0199c3f9888b5c5120
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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