Lithium Hydroxide → HCID 66699147, compound

HRID 1096040Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:23])[C:9]([C:15]2[S:19][C:18]([C:20]#[N:21])=[C:17]([CH3:22])[CH:16]=2)([OH:14])[C:10]([F:13])([F:12])[F:11])=[C:4]([Cl:24])[CH:3]=1.[F:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][C:31]=1[C:32]([O:34]C)=[O:33].[Li+].[OH-]>>[Cl:24][C:4]1[CH:3]=[C:2]([C:28]2[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[C:26]([F:25])[CH:27]=2)[CH:7]=[CH:6][C:5]=1[CH:8]([CH3:23])[C:9]([C:15]1[S:19][C:18]([C:20]#[N:21])=[C:17]([CH3:22])[CH:16]=1)([OH:14])[C:10]([F:13])([F:12])[F:11]

Participants

Reactant 3

HCID 3939Lithium Hydroxide

HCID 27828183-Fluoro-4-(methoxycarbonyl)benzeneboronic acid

HCID 66699185HCID 66699185, compound

Product 1

HCID 66699147HCID 66699147, compound

Procedure

The compound was prepared in analogy to Example 60, step 2, from 5-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-thiophene-2-carbonitrile and 3-fluoro-4-methoxycarbonylphenylboronic acid (CAS Reg. No. 505083-04-5). The resulting ester was hydrolyzed by addition of aqueous LiOH solution (1N) to the reaction mixture. Light yellow solid. MS (m/e, ISP neg. ion)=496.3 [M−H+].

Sources & evidence

ORD record: ord-6beefcd881874ab4818b3c247dbf3f65
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138189B2

Reaction notes

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