4-Fluorobenzyl bromide → HCID 11852796, compound

HRID 902512Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:28])[NH:8][C:9]2[C:13]([C:14]=1[N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[O:22])[CH2:17][CH2:16]1)=[CH:12][S:11][CH:10]=2)=[O:5])[CH3:2].[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Br)=[CH:32][CH:31]=1>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:28])[N:8]([CH2:34][C:33]2[CH:36]=[CH:37][C:30]([F:29])=[CH:31][CH:32]=2)[C:9]2[C:13]([C:14]=1[N:15]1[CH2:16][CH2:17][N:18]([C:21]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[O:22])[CH2:19][CH2:20]1)=[CH:12][S:11][CH:10]=2)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 680214-Fluorobenzyl bromide

HCID 59702104HCID 59702104, compound

Product 1

HCID 11852796HCID 11852796, compoundYield 54%

Procedure

The compound was prepared from 5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester (40) and 4-fluorobenzylbromide by applying general procedure A. Yield 54%; MP 227° C. 1H NMR (400 MHz, DMSO-d6) δ 1.27 (t, J=7.2 Hz, 3H), 3.30 (m, 4H), 3.83 (m, 4H), 4.27 (q, J=7.2 Hz, 2H), 5.18 (s, 2H), 7.14-7.17 (m, 3H), 7.20 (d, J=3.2 Hz, 1H), 7.33 (m, 2H), 7.46 (dd, J=1.2, 4.8 Hz, 1H), 7.80 (dd, J=1.2, 4.8 Hz, 1H), 8.13 (d, J=3.2 Hz, 1H) ppm; MS m/z=526 amu (M++1). Anal. (C26H24FN3O4S2) C, H, N.

Sources & evidence

ORD record: ord-ceb5486dacf04c588a5f6a0f15490179
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365200B2

Reaction notes

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