Potassium Carbonate → 4-(3-(3,6-Dihydro-2H-thiopyran-4-YL)pyrazin-2-yloxy)-N-methoxy-N-methylbenzamide

HRID 887465Notes

Reaction equation

Cl[C:2]1[C:3]([O:8][C:9]2[CH:20]=[CH:19][C:12]([C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][N:7]=1.[S:21]1[CH2:26][CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[S:21]1[CH2:22][CH:23]=[C:24]([C:2]2[C:3]([O:8][C:9]3[CH:20]=[CH:19][C:12]([C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14])=[CH:11][CH:10]=3)=[N:4][CH:5]=[CH:6][N:7]=2)[CH2:25][CH2:26]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-(3-chloropyrazin-2-yloxy)-N-methoxy-N-methylbenzamide (1.4 g, 4.77 mmol), 2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.132 g, 5.01 mmol), potassium carbonate (1.976 g, 14.30 mmol), and bis(tri-tert-butylphosphine)palladium(0) (0.244 g, 0.477 mmol) in p-dioxane/H2O (10:1, 11 ml) was heated to 120° C. in 4 h, cooled, taken up in H2O, extracted with EtOAc (3×), dried over MgSO4, concentrated and purified by ISCO (50% EtOAc/hexanes) to give the titled compound. MS [M+1]: 358.1.

Workup

temperaturecooled
extractionextracted with EtOAc (3×)
dry with materialdried over MgSO4
concentrationconcentrated
custompurified by ISCO (50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-77db4f685f354cdca3c86f8727a38f4a
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247418B2

Reaction notes

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