Cesium carbonate → 3'-Chloro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-biphenyl-4-carboxylic acid

HRID 1095904Notes

Reaction equation

HRID 1095904 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:22])[C:9]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=2)([OH:14])[C:10]([F:13])([F:12])[F:11])=[C:4]([Cl:23])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:30]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)([OH:32])=[O:31]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:23][C:4]1[CH:3]=[C:2]([C:36]2[CH:37]=[CH:38][C:33]([C:30]([OH:32])=[O:31])=[CH:34][CH:35]=2)[CH:7]=[CH:6][C:5]=1[CH:8]([CH3:22])[C:9]([OH:14])([C:15]1[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=1)[C:10]([F:13])([F:12])[F:11]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 3121834-Carboxyphenylboronic AcidHCID 574212913-(4-Bromo-2-chloro-phenyl)-1,1,1-trifluoro-2-(2-methyl-pyridin-4-yl)-butan-2-ol

Product 1

HCID 469401113'-Chloro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-biphenyl-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(4-bromo-2-chloro-phenyl)-1,1,1-trifluoro-2-(2-methyl-pyridin-4-yl)-butan-2-ol (10 mg), Pd(PPh3)4 (3 mg), Cs2CO3 (24 mg) and 4-carboxybenzeneboronic acid (CAS Reg. No. 14047-29-1, 8 mg) in dioxane (2 ml) was heated for 30 min at 160° C. in a microwave oven. The mixture was purified by prep. HPLC (C18-column, solvent gradient 30-98% CH3CN in 0.1% HCOOH[aq]) to give the title compound (3 mg) as a light yellow solid. MS (m/e)=450.1 [M+H+].

Workup

  1. customThe mixture was purified by prep

Sources & evidence

ORD record
ord-774a95fcbb2348589d9c49e599dc2a85
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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