2-Bromo-1-(thiophen-3-yl)ethan-1-one → 2-(3-{[(4-Fluorophenyl)sulfonyl]methyl}azetidin-1-yl)-1-(3-thienyl)ethanone

HRID 10231Notes

Reaction equation

HRID 10231 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH:13]2[CH2:16][NH:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Br[CH2:18][C:19]([C:21]1[CH:25]=[CH:24][S:23][CH:22]=1)=[O:20]>>[F:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH:13]2[CH2:16][N:15]([CH2:18][C:19]([C:21]3[CH:25]=[CH:24][S:23][CH:22]=3)=[O:20])[CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 27763792-Bromo-1-(thiophen-3-yl)ethan-1-oneHCID 219783933-{[(4-Fluorophenyl)sulfonyl]methyl}azetidine hydrochloride

Product 1

HCID 219784012-(3-{[(4-Fluorophenyl)sulfonyl]methyl}azetidin-1-yl)-1-(3-thienyl)ethanone

Procedure

Prepared according to the method of Example 2 using 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (Example 1 Step 4) and 2-bromo-1-(3-thienyl)ethanone. 1H NMR (500 MHz, d6-DMSO) δ 10.51 (1H, s), 8.52 (1H, s), 7.96 (2H, dd, J=5.1, 8.7 Hz), 7.72 (1H, dd, J=2.8, 5.0 Hz), 7.55 (2H, t, J=8.8 Hz), 7.49 (1H, d, J=4.3 Hz), 4.91 (2H, s), 4.19 (2H, s), 4.00 (2H, s), 3.82 (2H, d, J=6.7 Hz), 3.10–3.03 (1H, m); m/z (ES+) 354 (M+H)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-65a05bfa22984a2caa4c5a8462a966c6
Source dataset
uspto-grants-2006_08
Patent number
US07094777B2

Reaction notes

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