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Pyridine → N-methoxy-1-(4-methoxybenzyl)-3-methyl-N-methyl-1H-indole-6-carboxamide

HRID 380408
ノート
印刷プレビュー

反応式

HRID 380408 の反応式
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17](Cl)=[O:18])[CH:15]=3)[C:10]([CH3:20])=[CH:9]2)=[CH:5][CH:4]=1.Cl.[CH3:24][NH:25][O:26][CH3:27].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:27][O:26][N:25]([CH3:24])[C:17]([C:14]1[CH:15]=[C:16]2[C:11]([C:10]([CH3:20])=[CH:9][N:8]2[CH2:7][C:6]2[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:12][CH:13]=1)=[O:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 226634601-(4-methoxybenzyl)-3-methyl-1H-indole-6-carbonyl chloride

生成物 1

HCID 22663398N-methoxy-1-(4-methoxybenzyl)-3-methyl-N-methyl-1H-indole-6-carboxamide収率 92.7%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A stirred solution of 1-(4-methoxybenzyl)-3-methyl-1H-indole-6-carbonyl chloride [2.8 g, Reference Example 42(b)] in chloroform (90 ml) at 0° C. was treated with N,O-dimethylhydroxylamine hydrochloride (0.982 g) and pyridine (1.55 ml). The solution was stirred at room temperature for 1 hour then evaporated. The residue was partitioned between dichloromethane (100 ml) and brine (50 ml). The organic layer was dried over sodium sulphate then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2, v/v) to yield the title compound (2.8 g).

後処理

  1. customthen evaporated
  2. customThe residue was partitioned between dichloromethane (100 ml) and brine (50 ml)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customthen evaporated
  5. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2

出典と根拠

ORDレコード
ord-7ad3664e5f754cc88167d4d33abfef7c
出典データセット
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06303600B1

反応ノート

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