Triethylamine → 1-(4-Fluorophenyl)-2-(3-{[(4-fluorophenyl)sulfonyl]methyl}azetidin-1-yl)ethanone

HRID 10204

Reaction equation

HRID 10204 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.CCN(CC)CC.BrC1C=CC=CC=1[CH2:31][C:32]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)=[O:33]>CC#N>[F:40][C:37]1[CH:38]=[CH:39][C:34]([C:32](=[O:33])[CH2:31][N:15]2[CH2:16][CH:13]([CH2:12][S:9]([C:6]3[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[CH2:14]2)=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 219783933-{[(4-Fluorophenyl)sulfonyl]methyl}azetidine hydrochlorideHCID 607992432-(2-Bromophenyl)-1-(4-fluorophenyl)ethan-1-one

Product 1

HCID 111760041-(4-Fluorophenyl)-2-(3-{[(4-fluorophenyl)sulfonyl]methyl}azetidin-1-yl)ethanoneYield 68.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (75 mg, 0.28 mmol) in MeCN (5 mL) was treated with Et3N (97 μL, 0.7 mmol) and 2-bromo-4′-fluorophenylacetophenone (68 mg, 0.31 mmol) and stirred for 30 min at room temperature. The reaction was evaporated and the residue dissolved in DCM and purified using silica chromatography. The column was eluted with 1% MeOH/DCM to give the title compound as a white solid (70 mg, 68%). 1H NMR (500 MHz, CDCl3) δ 2.94–2.99 (1H, m), 3.10 (2H, t, J=7.4 Hz), 3.42 (2H, d, J=7.4 Hz), 3.62 (2H, t, J=7.4 Hz), 3.87 (2H, s), 7.12 (2H, t, J=8.8 Hz), 7.25 (2H, t, J=8.6 Hz), 7.90–7.94 (4H, m). m/z (ES+) 366 (M+H)+.

Workup

  1. customThe reaction was evaporated
  2. dissolutionthe residue dissolved in DCM
  3. custompurified
  4. washThe column was eluted with 1% MeOH/DCM

Sources & evidence

ORD record
ord-f6b68d0e61a241a69a6d42d86632ab49
Source dataset
uspto-grants-2006_08
Patent number
US07094777B2

Linked notes

Loading…