4-Hydroxyphenylboronic acid → 1-Cyclohexyl-3-(3,5-dichloro-4'-hydroxy-biphenyl-4-ylmethyl)-pyrrolidin-2-one

HRID 2235213Notes

Reaction equation

HRID 2235213 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([CH2:14][CH:15]2[CH2:19][CH2:18][N:17]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:16]2=[O:26])=[C:9]([Cl:27])[CH:8]=1)(=O)=O.[OH:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1>>[CH:20]1([N:17]2[CH2:18][CH2:19][CH:15]([CH2:14][C:10]3[C:11]([Cl:13])=[CH:12][C:7]([C:34]4[CH:35]=[CH:36][C:31]([OH:30])=[CH:32][CH:33]=4)=[CH:8][C:9]=3[Cl:27])[C:16]2=[O:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 27343604-Hydroxyphenylboronic acidHCID 592994213,5-Dichloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)phenyl trifluoromethanesulfonate

Product 1

HCID 592993351-Cyclohexyl-3-(3,5-dichloro-4'-hydroxy-biphenyl-4-ylmethyl)-pyrrolidin-2-oneYield 91%

Procedure

Using the procedure to synthesize Example 81 and using reagents 3,5-dichloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)phenyl trifluoromethanesulfonate (Example 240) (750 mg, 1.58 mmol) and 4-hydroxyphenylboronic acid (650 mg, 4.7 mmol) affords 600 mg (91%) of the title compound: Mass spectrum (apci) m/z=418.2 (M+H—HCl).

Workup

  1. customto synthesize Example 81

Sources & evidence

ORD record
ord-42ff8be24dd04f1d939c83fab747db3f
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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