Sodium Carbonate → 1-Cyclohexyl-3-[2,6-dichloro-4-(1-isobutyl-1H-pyrazol-4-yl)-benzyl]-pyrrolidin-2-one

HRID 2235331Notes

Reaction equation

HRID 2235331 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.[CH2:30]([N:34]1[CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:36]=[N:35]1)[CH:31]([CH3:33])[CH3:32].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[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:37]4[CH:36]=[N:35][N:34]([CH2:30][CH:31]([CH3:33])[CH3:32])[CH:38]=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

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27593921-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 592994213,5-Dichloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)phenyl trifluoromethanesulfonate

Product 1

HCID 592993031-Cyclohexyl-3-[2,6-dichloro-4-(1-isobutyl-1H-pyrazol-4-yl)-benzyl]-pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Using the method of Example 81 and using 3,5-dichloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)phenyl trifluoromethanesulfonate (Example 240) (1.459 g, 3.07 mmol), 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.3 g, 9.23 mmol) tetrakis(triphenylphosphine)palladium (0.355 g, 0.307 mmol), dimethoxyethane (15 mL) and sodium carbonate (2M, 5.4 mL) gives the title compound. Purify the crude material over silica gel (1/1 hexane in ethyl acetate) to yield 1.047 g (76%) of the title compound: mass spectrum (m/z): 450(M+2).

Sources & evidence

ORD record
ord-bc2d54e54d2f4d2983e3da2dd964090e
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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