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

HRID 21589노트

반응식

HRID 21589 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 58012-AminophenolHCID 8471TriethylamineHCID 13840811HCID 13840811, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7c4604f69f85470bb595a3b7268272d2
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424329

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