Water → N-(2-Hydroxyphenyl)-5-methoxy-3-(1-methylethoxy)-1-phenyl-1H-indole-2-carboxamide

HRID 21589ノート

反応式

HRID 21589 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C:18]([OH:20])=O)=[C:6]2[O:21][CH:22]([CH3:24])[CH3:23].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[OH:32].C(N(CC)CC)C.O>O1CCCC1>[OH:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[NH:25][C:18]([C:7]1[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:5]([C:6]=1[O:21][CH:22]([CH3:24])[CH3:23])=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)=[O:20]

参加物

6

反応物 4

HCID 962WaterHCID 58012-AminophenolHCID 8471TriethylamineHCID 13840811HCID 13840811、化合物

生成物 1

HCID 19933215N-(2-Hydroxyphenyl)-5-methoxy-3-(1-methylethoxy)-1-phenyl-1H-indole-2-carboxamide収率 70%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

The procedure described in Example 16 is used to prepare the acyl chloride of 5-methoxy-3-(1-methylethoxy)-1-phenyl-1H-indole-2-carboxylic acid (4.0 g, 12 mmol). A solution of the crude acyl chloride in 45 mL of tetrahydrofuran is cooled in ice and treated dropwise with a solution of 2-aminophenol (1.3 g, 12 mmol) in 20 mL of tetrahydrofuran, followed by dropwise addition of triethylamine (1.7 mL, 1.2 g, 12 mmol). The mixture is stirred at room temperature for 2 hours and added to 300 mL of water. The mixture is extracted with dichloromethane, and the combined organic layers are washed with brine, dried (anhydrous sodium sulfate), and evaporated. Trituration of the residue with tert-butyl methyl ether yields 3.5 g (69%) of product; mp 168°-170° C.

後処理

  1. extractionThe mixture is extracted with dichloromethane
  2. washthe combined organic layers are washed with brine
  3. dry with materialdried (anhydrous sodium sulfate)
  4. customevaporated

出典と根拠

ORDレコード
ord-7c4604f69f85470bb595a3b7268272d2
出典データセット
uspto-grants-1995_06
特許番号
US05424329

反応ノート

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