Triethylamine → {6-[4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-indol-1-yl}-acetic acid methyl ester

HRID 605532노트

반응식

HRID 605532 반응식
[CH3:1][O:2][C:3](=[O:34])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10](Br)=[C:11]([S:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)(=[O:16])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1.C(N(CC)CC)C>[Pd].[C]>[CH3:1][O:2][C:3](=[O:34])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([S:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)(=[O:15])=[O:16])[CH:12]=2)[CH:7]=[CH:6]1

참가 물질

4

반응물 2

HCID 8471TriethylamineHCID 57565263HCID 57565263, 화합물

생성물 1

HCID 57565246{6-[4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-indol-1-yl}-acetic acid methyl ester수율 83.1%

시약·촉매·용매 1

HCID 178418390HCID 178418390, 화합물촉매

실험 절차

{5-Bromo-6-[4-(4-trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-indol-1-yl}-acetic acid methyl ester (135 mg, 0.24 mmol), triethylamine (40 μL, 0.29 mmol) and 10% Pd/carbon (cat) were stirred under an atmosphere of hydrogen until all the starting material was gone. The reaction was then filtered through celite, concentrated and purified by flash column chromatography (60% hexanes in ethyl acetate) to afford {6-[4-(4-trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-indol-1-yl}-acetic acid methyl ester (96 mg, 83%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.76 (d, 1H) 7.75 (d, 1H), 7.51 (dd, 1H), 7.44 (dd, 2H), 7.31 (d, 1H), 6.84 (d, 2H), 6.67 (d, 1H), 4.11 (dd, 2H), 3.78 (s, 3H), 3.33 (m, 4H), 3.16 (m, 4H).

후처리

  1. filtrationThe reaction was then filtered through celite,
  2. concentrationconcentrated
  3. custompurified by flash column chromatography (60% hexanes in ethyl acetate)

출처 및 근거

ORD 기록
ord-29cf9cec64464c4fbf338d78431da414
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915253B2

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