Lithium Hydroxide → HCID 59507374, compound

HRID 2096798Notes

Reaction equation

HRID 2096798 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:27])[C:9]([C:15]2[CH:26]=[CH:25][C:18]3[N:19]([CH3:24])[C:20](=[O:23])[N:21]([CH3:22])[C:17]=3[CH:16]=2)([OH:14])[C:10]([F:13])([F:12])[F:11])=[C:4]([Cl:28])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[F:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][C:41]=1[C:42]([O:44]C)=[O:43].[Li+].[OH-]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(O)=O>[Cl:28][C:4]1[CH:3]=[C:2]([C:38]2[CH:39]=[CH:40][C:41]([C:42]([OH:44])=[O:43])=[C:36]([F:35])[CH:37]=2)[CH:7]=[CH:6][C:5]=1[CH:8]([CH3:27])[C:9]([C:15]1[CH:26]=[CH:25][C:18]2[N:19]([CH3:24])[C:20](=[O:23])[N:21]([CH3:22])[C:17]=2[CH:16]=1)([OH:14])[C:10]([F:13])([F:12])[F:11]

Participants

8

Reactant 4

HCID 3939Lithium HydroxideHCID 10796Cesium carbonateHCID 27828183-Fluoro-4-(methoxycarbonyl)benzeneboronic acidHCID 67545637HCID 67545637, compound

Product 1

HCID 59507374HCID 59507374, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 284Formic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (40 mg), dichloro[1,1′-bis(diphenylphosphino) ferrocene]palladium(II) (7 mg), Cs2CO3 (82 mg) and 3-fluoro-4-methoxycarbonylphenylboronic acid (CAS Reg. No. 505083-04-5, 33 mg) in dioxane (2 ml) was heated at 80° C. for 20 min in a sealed tube. 1N aqeuos LiOH solution (1 ml) was added and stirred for 20 min at room temperature. The mixture was acidified with HCOOH and then purified by prep. HPLC (C18-column, solvent gradient 30-98% CH3CN in 0.1% HCOOH[aq]) to give the title compound (32 mg) as a yellow solid. MS (m/e)=537.2 [M+H+].

Workup

  1. additionwas added
  2. custompurified by prep

Sources & evidence

ORD record
ord-7b29ccd9eec64c2e8fa1f557011c08c5
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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