Ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate → 3'-Chloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-2-carboxylic acid ethyl ester

HRID 2235246Notes

Reaction equation

HRID 2235246 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.[CH2:22]([O:24][C:25](=[O:41])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B1OC(C)(C)C(C)(C)O1)[CH3:23]>>[CH2:22]([O:24][C:25]([C:26]1[C:27]([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:28][CH:29]=[CH:30][CH:31]=1)=[O:41])[CH3:23]

Participants

3

Reactant 2

HCID 2773962Ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 116822063-(4-Bromo-2-chlorobenzyl)-1-cyclohexylpyrrolidin-2-one

Product 1

HCID 592993403'-Chloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-2-carboxylic acid ethyl esterYield 48.3%

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 ethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (560 mg, 2.0 mmol) affords 287 mg (48%) of the title compound: Mass spectrum (apci) m/z=440.2 (M+H).

Workup

  1. customto synthesize Example 81

Sources & evidence

ORD record
ord-2a58b6346c4243fd84e0cbd6a031c573
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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