1-Methyl-1H-indole-3-carbaldehyde → HCID 58779044, 화합물

HRID 1372757노트

반응식

HRID 1372757 반응식
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[CH:4]=1)=[O:2].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:16]([F:25])[C:15]=1O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CO>[F:25][C:16]1[C:15]2[O:2][C:1]([C:3]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]([CH3:12])[CH:4]=3)=[N:13][C:14]=2[CH:19]=[CH:18][C:17]=1[CH2:20][C:21]([O:23][CH3:24])=[O:22]

참가 물질

5

반응물 3

HCID 878941-Methyl-1H-indole-3-carbaldehydeHCID 12217721Iodo benzene diacetateHCID 17859032Methyl (4-amino-2-fluoro-3-hydroxyphenyl)acetate

생성물 1

HCID 58779044HCID 58779044, 화합물수율 50.8%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

In methanol (50 ml), 3-formyl-1-methylindole (796 mg, 5.0 mmol), methyl (4-amino-2-fluoro-3-hydroxyphenyl)acetate (1.0 g, 5.0 mmol) and Molecular Sieves 4A (10 g) were stirred at room temperature for 5 hours and then, at 70° C. for 3 hours. The reaction mixture was cooled to room temperature and iodobenzene diacetate (5.0 mmol) was added thereto. After stirring at room temperature for 14 hours, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (3/1) eluate fractions, methyl 7-fluoro-2-(1-methyl-3-indolyl)-6-benzoxazolylacetate (860 mg, including impurities) was obtained as a pale brown solid. The compound was provided for the subsequent reaction without further purification.

후처리

  1. distillationthe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (3/1) eluate fractions

출처 및 근거

ORD 기록
ord-99c7543ef46a426badce607a261086ba
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157487B2

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