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

HRID 10204

반응식

HRID 10204 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-f6b68d0e61a241a69a6d42d86632ab49
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094777B2

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