2-Ethylaniline → N-(2-ethylphenyl)-2-(1H-indol-3-yl)-2-oxoacetamide

HRID 885100

반응식

HRID 885100 반응식
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2].CCN(C(C)C)C(C)C.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([C:28](=[O:32])[C:29](Cl)=[O:30])=[CH:20]1>CN(C=O)C>[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][C:29](=[O:30])[C:28]([C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH:19][CH:20]=1)=[O:32])[CH3:2]

참가 물질

5

반응물 3

HCID 113572-EthylanilineHCID 81531DiisopropylethylamineHCID 899523-Indoleglyoxylyl chloride

생성물 1

HCID 3620873N-(2-ethylphenyl)-2-(1H-indol-3-yl)-2-oxoacetamide수율 39%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a stirring solution of 2-ethyl-aniline (74 μL, 0.6 mmol) and DIEA (110 μL, 0.6 mmol) in DMF (1 mL) was added a solution of (1H-indol-3-yl)-oxo-acetyl chloride (62 mg, 0.3 mmol) in DMF (1 mL). The reaction was stirred at room temperature for 2 hours, then filtered and purified by HPLC (10-99% CH3CN/H2O) to yield the product N-(2-ethyl-phenyl)-2-(1H-indol-3-yl)-2-oxo-acetamide (34 mg, 39%). HPLC ret. time 3.50 min, 10-99% CH3CN, 5 min run; 1H NMR (400 MHz, DMSO-d6) δ 12.33 (s, 1H), 10.14 (s, 1H), 8.79 (d, J=3.2 Hz, 1H), 8.30 (m, 1H), 7.57 (m, 2H), 7.33-7.21 (m, 5H), 2.67 (q, J=7.6 Hz, 2H), 1.17 (t, J=7.6 Hz, 3H); ESI-MS m/z 293.1 (MH+).

후처리

  1. filtrationfiltered
  2. custompurified by HPLC (10-99% CH3CN/H2O)

출처 및 근거

ORD 기록
ord-f792cc0190654744b2ec46531b7c7f37
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242149B2

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