Lithium Hydroxide → HCID 59507374, compound
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
Product 1
Reagents, catalysts & solvents 3
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 aqueous 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
- custompurified by prep
Sources & evidence
- ORD record
- ord-70d87675e9544c68b8f935694957442d
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268820B2
Reaction notes
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