Triethylamine → 3-[7,8,9,10-tetrahydro-6H-azepino[1,2-a]indol-11-yl]-3-(1-methyl-3-indolyl)furan-2,5-dione

HRID 863695ノート

反応式

HRID 863695 の反応式
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[C:10]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:11]12.[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH2:31][C:32]([OH:34])=[O:33])=[CH:23]1.C(N(CC)CC)C>ClCCl>[CH:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9]([C:31]1([C:24]3[C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:22]([CH3:21])[CH:23]=3)[CH2:2][C:1](=[O:5])[O:34][C:32]1=[O:33])=[C:10]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:11]12

参加物

6

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2541662-(1-methyl-1H-indol-3-yl)acetic acidHCID 111167347,8,9,10-tetrahydro-6H-azepino[1,2-a]indole

生成物 1

HCID 196963163-[7,8,9,10-tetrahydro-6H-azepino[1,2-a]indol-11-yl]-3-(1-methyl-3-indolyl)furan-2,5-dione収率 22.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

1.5 g of oxalyl chloride were added dropwise to an ice-cold solution of 2.0 g of 7,8,9,10-tetrahydro-6H-azepino[1,2-a]indole (J. Org. Chem. 33, 1968, 4286) in 50 ml of dichloromethane. The mixture was stirred for 2 hours. The solvent was removed in a vacuum and the residue was dissolved in dichloromethane. The solution obtained was added to a solution of 2.2 g of 1-methyl-3-indolylacetic acid and 2.73 g of triethylamine in 50 ml of dichloromethane. The mixture was stirred and then concentrated. The residue was chromatographed on silica gel with dichloromethane and there was obtained 1.0 g of 3-[7,8,9,10-tetrahydro-6H-azepino[1,2-a]indol-11-yl]-3-(1-methyl-3-indolyl)furan-2,5-dione of melting point 257°-259° C.

後処理

  1. customThe solvent was removed in a vacuum
  2. dissolutionthe residue was dissolved in dichloromethane
  3. customThe solution obtained
  4. stirringThe mixture was stirred
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel with dichloromethane

出典と根拠

ORDレコード
ord-b40e585f1f6b4f499d8db2815a94f907
出典データセット
uspto-grants-1998_02
特許番号
US05721245

反応ノート

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