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

HRID 1362430ノート

反応式

HRID 1362430 の反応式
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]

参加物

8

反応物 6

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

生成物 1

HCID 12461785N-methyl-1H-indole-2-carboxamide収率 153.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)

後処理

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

出典と根拠

ORDレコード
ord-ec51eab26da8492aa2c1e886d434cd7b
出典データセット
uspto-grants-2011_02
特許番号
US07879872B2

反応ノート

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