Sodium Carbonate → HCID 59299429, compound

HRID 2235333Notes

Reaction equation

HRID 2235333 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.[S:30]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31]1.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:9]([Cl:27])=[CH:8][C:7]([C:32]4[CH:33]=[CH:34][S:30][CH:31]=4)=[CH:12][C:11]=3[Cl:13])[C:16]2=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 592994213,5-Dichloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)phenyl trifluoromethanesulfonate

Product 1

HCID 59299429HCID 59299429, compound

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) (1.485 g, 3.31 mmol), thiophene-3-boronic acid (1.2 g, 9.39 mmol) tetrakis(triphenylphosphine)palladium (0.362 g, 0.3.13 mmol), dimethoxyethane (15 mL) and sodium carbonate (2M, 5.5 mL) gives the title compound. Purify the crude material over silica gel (4/1 hexane in ethyl acetate) to yield 1.109 g (87%) of the title compound: mass spectrum (m/z): 410(M+2).

Sources & evidence

ORD record
ord-96b7b2c6753a426abf749eaec04e5658
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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