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

HRID 40170
Notes
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Reaction equation

HRID 40170 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 59762310Methyl 3-(3,4-Difluorobenzylcarbamoyl)-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 6343EthanethiolSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b079c2f2f2ca4ed183a22a6b5cd81fa1
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524917B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes