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

HRID 1253618
Notes
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Reaction equation

HRID 1253618 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11514065Ethyl 4-hydroxy-2-methylbenzofuran-6-carboxylateHCID 594833125-chloro-N-ethyl-N-methylpyrazine-2-carboxamide

Product 1

HCID 59483314Ethyl 4-(5-(ethyl(methyl)carbamoyl)pyrazin-2-yloxy)-2-methylbenzofuran-6-carboxylate

Reagents, catalysts & solvents 2

HCID 6342Acetonitrile
Solvent
HCID 8857Ethyl AcetateSolvent

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

  1. filtrationfiltered
  2. concentrationThe organic layer was concentrated
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes