(4-((Tert-butoxy)carbonyl)phenyl)boronic acid → 3'-Chloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-carboxylic acid tert-butyl ester

HRID 2235248Notes

Reaction equation

HRID 2235248 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][N:9]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[C:8]2=[O:18])=[C:4]([Cl:21])[CH:3]=1.[C:22]([O:26][C:27]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>>[C:22]([O:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([C:2]2[CH:20]=[CH:19][C:5]([CH2:6][CH:7]3[CH2:11][CH2:10][N:9]([CH:12]4[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]4)[C:8]3=[O:18])=[C:4]([Cl:21])[CH:3]=2)=[CH:31][CH:30]=1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

3

Reactant 2

HCID 2773301(4-((Tert-butoxy)carbonyl)phenyl)boronic acidHCID 116822063-(4-Bromo-2-chlorobenzyl)-1-cyclohexylpyrrolidin-2-one

Product 1

HCID 592993213'-Chloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-carboxylic acid tert-butyl esterYield 78.3%

Procedure

Using the procedure to synthesize Example 81 and using reagents 3-(4-bromo-2-chloro-benzyl)-1-cyclohexyl-pyrrolidin-2-one (500 mg, 1.35 mmol) and 4-(tert-butoxycarbonyl)phenylboronic acid (900 mg, 4.0 mmol) affords 495 mg (78%) of the title compound: Mass spectrum (apci) m/z=468.2 (M+H).

Workup

  1. customto synthesize Example 81

Sources & evidence

ORD record
ord-992fb4d318a84a3c9fbd45b98f98a556
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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