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

HRID 10204

反応式

HRID 10204 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-f6b68d0e61a241a69a6d42d86632ab49
出典データセット
uspto-grants-2006_08
特許番号
US07094777B2

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