Lithium Hydroxide → HCID 67021164, compound

HRID 735479Notes

Reaction equation

HRID 735479 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]([C:16]3[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=3)=[C:14]3[C:9]([C:10]([C:23]([F:26])([F:25])[F:24])=[CH:11][CH:12]=[CH:13]3)=[N:8]2)=[C:4]([F:29])[CH:3]=1.C[O:31][C:32](=[O:41])[CH:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Li+].[OH-]>ClCCl.C1COCC1.O>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]([C:16]3[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=3)[O:22][CH:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:32]([OH:41])=[O:31])=[C:14]3[C:9]([C:10]([C:23]([F:25])([F:26])[F:24])=[CH:11][CH:12]=[CH:13]3)=[N:8]2)=[C:4]([F:29])[CH:3]=1

Participants

8

Reactant 4

HCID 3939Lithium HydroxideHCID 10796Cesium carbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 67021271HCID 67021271, compound

Product 1

HCID 67021164HCID 67021164, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-[2-(4-Chloro-2-fluoro-benzyl)-7-trifluoromethyl-2H-indazol-3-yl]-phenol (25 mg, 1 eq) was treated with bromo-phenyl-acetic acid methyl ester (41 mg, 3 eq) and cesium carbonate (95 mg, 5 eq) in dichloromethane (2 mL) until the reaction mixture was completed as judged by TLC. Water was added followed by extraction with dichloromethane. Subsequently, the ester was hydrolyzed in aq. LiOH (1M, 15 eq)/THF 1:1. Purification by flash chromatography, eluent: 2-5% methanol in dichloromethane, afforded the title compound in 55% yleld.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. customPurification by flash chromatography, eluent

Sources & evidence

ORD record
ord-e5460cd6a1dd494a94534dc3b5c0b0e3
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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