Benzoyl chloride → methyl 2-(4-chlorobenzoyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

HRID 2369344ノート

反応式

HRID 2369344 の反応式
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH:3]([C:14]([O:16][CH3:17])=[O:15])[NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[C:18]([Cl:26])(=O)[C:19]1C=CC=C[CH:20]=1.C(N(CC)CC)C.[CH2:34]1[CH2:38][O:37][CH2:36][CH2:35]1>>[Cl:26][C:18]1[CH:36]=[CH:35][C:34]([C:38]([N:2]2[CH:3]([C:14]([O:16][CH3:17])=[O:15])[CH2:4][C:5]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[NH:7][C:6]=3[CH2:1]2)=[O:37])=[CH:20][CH:19]=1

参加物

5

反応物 4

HCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 1777282,3,4,9-Tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester

生成物 1

HCID 15626677methyl 2-(4-chlorobenzoyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

実験手順

A mixture of methyl 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (6.9 g, 30 mmol), benzoylchloride (4.2 g, 30 mmol) and triethylamine (4.8 mL) in anhydrous THF (150 mL) was refluxed for 9 h. It was concentrated and diluted with water. The solid precipitated was collected by filtration, the solid cake was washed successfully with water and hexane and dried to give methyl 2-(4-chlorobenzoyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate, 9.0 g (82%); mp 243-244° C. (lit.19 mp 245-246° C.). 1H NMR (DMSO-d6) δ 3.10 (1H, m, CH2), 3.35 (1H, m, CH2), 3.55 and 3.65 (3H, s, COOMe), 4.41 and 5.18 (1H, d, J=17.4 Hz, NCH2), 4.51 and 4.64 (1H, d, J=16.4 Hz, NCH2), 4.88 and 5.82 (1H, d, J=5.4 Hz, CH), 6.96-6.99 (1H, m, ArH), 7.03-7.08 (1H, m, ArH), 7.25-7.32 (1H, m, ArH), 7.42-7.60 (5H, m, 5×ArH), 10.65 and 10.95 (1H, s, exchangeable NH).

後処理

  1. temperaturewas refluxed for 9 h
  2. concentrationIt was concentrated
  3. additiondiluted with water
  4. customThe solid precipitated
  5. filtrationwas collected by filtration
  6. washthe solid cake was washed successfully with water and hexane
  7. customdried

出典と根拠

ORDレコード
ord-4f942f0800fb45cabd9d6cba5683b246
出典データセット
uspto-grants-2014_04
特許番号
US08703951B2

反応ノート

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