1,2-Dichloroethane → N-methyl-1H-indole-2-carboxamide

HRID 1362430노트

반응식

HRID 1362430 반응식
C(Cl)CCl.[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:14]([OH:16])=O.CN.C(O)C.C1C=CC2N(O)N=[N:28][C:26]=2C=1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:26][NH:28][C:14]([C:6]1[NH:5][C:13]2[C:8]([CH:7]=1)=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:16]

참가 물질

8

반응물 6

HCID 111,2-DichloroethaneHCID 702EthanolHCID 6329MethylamineHCID 72899Indole-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

생성물 1

HCID 12461785N-methyl-1H-indole-2-carboxamide수율 153.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

EDC (7.7 g, 40.3 mmol) was added to a solution of indole-2-carboxylic acid (5 g, 13.1 mmol), methylamine, 33% in ethanol (5.6 mL, 15.5 mmol), HOBT (4.1 g, 13.1 mmol) and DIPEA (2.1 mL, 12.4 mmol) in THF, anhydrous (45 mL) and stirred overnight. The crude mixture was evaporated in vacuo and chromatographed over silica eluting with methanol/dichloromethane (0-2%) to afford the title compound (3.51 g, 66%). 1H NMR (300 MHz, DMSO-d6) δ 11.53 (s, 1H), 8.43 (s, 1H), 7.57 (d, J=7.9 Hz, 1H), 7.39 (d, J=8.2 Hz, 1H), 7.15 (t, J=8.2 Hz, 1H), 7.03 (s, 1H), 6.98 (t, J=7.9 Hz, 1H), 2.79 (d, J=4.7 Hz, 3H)

후처리

  1. customThe crude mixture was evaporated in vacuo
  2. customchromatographed over silica eluting with methanol/dichloromethane (0-2%)

출처 및 근거

ORD 기록
ord-ec51eab26da8492aa2c1e886d434cd7b
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879872B2

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