3-(Ethoxycarbonyl)-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → 3'-Chloro-4-fluoro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-propyl]-biphenyl-3-carboxylic acid ethyl ester

HRID 2386815Notes

Reaction equation

HRID 2386815 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:26])[C:9]([C:15]2[CH:16]=[CH:17][C:18]3[O:22][C:21](=[O:23])[N:20]([CH3:24])[C:19]=3[CH:25]=2)([OH:14])[C:10]([F:13])([F:12])[F:11])=[C:4]([Cl:27])[CH:3]=1.[CH2:28]([O:30][C:31]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][C:38]=1[F:39])=[O:32])[CH3:29]>>[CH2:28]([O:30][C:31]([C:33]1[CH:34]=[C:35]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([CH3:26])[C:9]([OH:14])([C:15]3[CH:16]=[CH:17][C:18]4[O:22][C:21](=[O:23])[N:20]([CH3:24])[C:19]=4[CH:25]=3)[C:10]([F:11])([F:12])[F:13])=[C:4]([Cl:27])[CH:3]=2)[CH:36]=[CH:37][C:38]=1[F:39])=[O:32])[CH3:29]

Participants

3

Reactant 2

HCID 249017713-(Ethoxycarbonyl)-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 666969815-[2-(4-Bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-3H-benzooxazol-2-one

Product 1

HCID 666969973'-Chloro-4-fluoro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-propyl]-biphenyl-3-carboxylic acid ethyl ester

Procedure

The title compound was prepared in analogy to Example 117 from 5-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-3H-benzooxazol-2-one (obtained in Example 116, step 8) by Suzuki coupling with 3-ethoxycarbonyl-4-fluoro-phenylboronic acid [CAS Reg. No. 874219-36-0]. MS (m/e)=552.3 [M+H+], MS (m/e)=506.1 [(M−CH3CH2O−)+].

Sources & evidence

ORD record
ord-217af853b62344e49ded16628e25430d
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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