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Aluminum(III) Chloride → 3-(3,4-Difluorobenzylcarbamoyl)-6-hydroxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylic Acid

HRID 40170
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HRID 40170 반응식
[Al+3].[Cl-].[Cl-].[Cl-].C[O:6][C:7]([C:9]1[N:10]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[C:11]2[C:16]([C:17]=1[C:18](=[O:29])[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[C:23]([F:28])[CH:22]=1)=[CH:15][CH:14]=[C:13]([O:30]C)[CH:12]=2)=[O:8]>CCS.C(Cl)Cl>[F:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[F:27])[CH2:20][NH:19][C:18]([C:17]1[C:16]2[C:11](=[CH:12][C:13]([OH:30])=[CH:14][CH:15]=2)[N:10]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[C:9]=1[C:7]([OH:8])=[O:6])=[O:29]
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참가 물질

5

반응물 2

HCID 6451240Aluminum(III) ChlorideHCID 59762310Methyl 3-(3,4-Difluorobenzylcarbamoyl)-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate2회

생성물 1

HCID 597623373-(3,4-Difluorobenzylcarbamoyl)-6-hydroxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylic Acid

시약·촉매·용매 2

HCID 6343Ethanethiol용매HCID 6344Dichloromethane
용매

실험 절차

General Procedure M. To a solution of AlCl3 (1.8 g, 13.5 mmol) in EtSH (25 ml) at room temperature was added a solution of methyl3-(3,4-difluorobenzylcarbamoyl)-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate (Compound 93, 1.26 g, 2.7 mmol) in CH2Cl2 (75 ml). The reaction was stirred for 2 h and was quenched with ice. The mixture was concentrated in vacuo, and the resulting white suspension in aqueous solution was acidified with 1M HCl and filtered. The cake was washed with H2O (×3), taken in MeOH, dried over MgSO4, and concentrated in vacuo to yield the title compound as a crude yellowish white solid contaminated with unknown inorganic product. The crude was used without further purification.

후처리

  1. customwas quenched with ice
  2. concentrationThe mixture was concentrated in vacuo
  3. filtrationfiltered
  4. washThe cake was washed with H2O (×3)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b079c2f2f2ca4ed183a22a6b5cd81fa1
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08524917B2

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