Iodo benzene diacetate → HCID 86592801, 화합물

HRID 1372754노트

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HRID 1372754 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[CH:12]=[O:13].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][C:16]=1O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CCO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[C:12]1[O:13][C:16]2[CH:17]=[C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:20][C:15]=2[N:14]=1

참가 물질

5

반응물 3

HCID 12217721Iodo benzene diacetateHCID 167237965-chloro-1-methyl-1H-indole-3-carbaldehydeHCID 17858854Methyl 2-(4-amino-3-hydroxyphenyl)acetate

생성물 1

HCID 86592801HCID 86592801, 화합물수율 60.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

In EtOH (9.0 ml), 5-chloro-1-methylindole-3-carbaldehyde (534 mg, 2.76 mmol) and methyl 4-amino-3-hydroxyphenylacetate (500 mg, 2.76 mmol) were stirred for hours. After iodobenzene diacetate (2.03 g, 6.31 mmol) was added to the reaction mixture and the mixture was stirred at room temperature for 1 hour, the solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (1:1, v/v) eluate fractions, a mixture (594 mg) of methyl (2-(5-chloro-1-methyl-3-indolyl)-6-benzoxazolyl)acetate and 5-chloro-1-methylindole-3-carboxaldehyde was obtained. To the resulting mixture were added THF (17 ml) and 0.25N NaOH (10.0 ml, 2.50 mmol) and the mixture was stirred at room temperature for 23 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. To the residue was added 1N HCl (10 ml), followed by extraction with chloroform-methanol (4:1, v/v). The extract was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent to give (2-(5-chloro-1-methyl-3-indolyl)-6-benzoxazolyl)acetic acid (88 mg, 9%) as a brown solid.

후처리

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (1:1

출처 및 근거

ORD 기록
ord-e5f5fdeeee46411ba4299e10dba6301f
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157487B2

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