Potassium Carbonate → Ethyl 4-(5-(ethyl(methyl)carbamoyl)pyrazin-2-yloxy)-2-methylbenzofuran-6-carboxylate

HRID 1253618Notes

Reaction equation

[OH:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:11])[O:10][C:6]=2[CH:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:24]1[N:25]=[CH:26][C:27]([C:30]([N:32]([CH2:34][CH3:35])[CH3:33])=[O:31])=[N:28][CH:29]=1>C(#N)C.C(OC(=O)C)C>[CH2:34]([N:32]([CH3:33])[C:30]([C:27]1[N:28]=[CH:29][C:24]([O:1][C:2]2[C:7]3[CH:8]=[C:9]([CH3:11])[O:10][C:6]=3[CH:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=2)=[N:25][CH:26]=1)=[O:31])[CH3:35]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 4-hydroxy-2-methylbenzofuran-6-carboxylate (I-1c: 2.25 g, 10.22 mmol), potassium carbonate (2.1 g, 15.3 mmol), 5-chloro-N-ethyl-N-methylpyrazine-2-carboxamide (SM-4: 2.04 g, 10.2 mmol) were mixed in acetonitrile (30 ml). The mixture was heated at 100° C. over night, after which time, the reaction mixture was diluted with ethylacetate (50 ml) and filtered. The organic layer was concentrated and purified by column chromatography on silica gel eluting with ethylacetate in heptanes 20-100% to afford ethyl 4-(5-(ethyl(methyl)carbamoyl)pyrazin-2-yloxy)-2-methylbenzofuran-6-carboxylate (I-7a: (3.9 g, 99.5%) as a gum.

Workup

filtrationfiltered
concentrationThe organic layer was concentrated
custompurified by column chromatography on silica gel eluting with ethylacetate in heptanes 20-100%

Sources & evidence

ORD record: ord-99b17c9acbfd46bb9021d801110ebe65
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455496B2

Reaction notes

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