Chloride → 1-methyl-N-[2-(6-methoxy-2-naphthyl)-2-oxoethyl]-1H-indole-3-carboxamide

HRID 2355124ノート

反応式

HRID 2355124 の反応式
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20](=[O:23])[CH2:21][NH3+:22])[CH:14]=[CH:13]2.[Cl-].[CH3:25][N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([C:35](Cl)=[O:36])=[CH:27]1>C(Cl)Cl>[CH3:25][N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([C:35]([NH:22][CH2:21][C:20]([C:15]2[CH:14]=[CH:13][C:12]3[C:17](=[CH:18][CH:19]=[C:10]([O:9][CH3:8])[CH:11]=3)[CH:16]=2)=[O:23])=[O:36])=[CH:27]1

参加物

6

反応物 4

HCID 312ChlorideHCID 8471TriethylamineHCID 151324411-Methyl-1H-indole-3-carbonyl chlorideHCID 866035202-(6-Methoxy-naphthalen-2-yl)-2-oxo-ethyl-ammonium

生成物 1

HCID 684532481-methyl-N-[2-(6-methoxy-2-naphthyl)-2-oxoethyl]-1H-indole-3-carboxamide収率 91%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

Triethylamine (3.2 mL, 22.8 mmol) in 30 mL of methylene chloride was added dropwise over 2 h to a mixture of 2-(6-methoxy-naphthalen-2-yl)-2-oxo-ethyl-ammonium; chloride (2.47 g, 11.4 mmol), prepared in step 3 of Example 1, and 1-methyl-1H-indole-3-carbonyl chloride (2.21 g, 11.4 mmol), prepared in the previous step, in 100 mL of methylene chloride at room temperature. After the addition of the reaction was stirred at room temperature for 16 h (overnight). The reaction was diluted with methylene chloride, extracted twice with 1N HCl, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 1-methyl-N-[2-(6-methoxy-2-naphthyl)-2-oxoethyl]-1H-indole-3-carboxamide (3.86 g, 91%) as a yellow solid, mp 177-180° C. Elemental Analysis for C23H20N2O3 Calc'd: C, 74.18; H, 5.41; N, 7.52. Found: C, 72.68; H, 5.34; N, 7.29

後処理

  1. additionAfter the addition of the reaction
  2. extractionextracted twice with 1N HCl
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-4ece98e047d14afea4e3a62e79910fc6
出典データセット
uspto-grants-2010_07
特許番号
US07754747B2

反応ノート

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