3-Chloro-N-methoxy-N-methylpyrazine-2-carboxamide → [4-(Benzyloxy)phenyl](3-chloropyrazin-2-yl)methanone

HRID 573311Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:8](N(OC)C)=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:8]([C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=2)=[O:9])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-chloro-N-methoxy-N-methylpyrazine-2-carboxamide (2.05 g) in THF (50 mL) was added dropwise [4-(benzyloxy)phenyl]magnesium bromide in THF (12 mL) at 0° C. After stirring at 0° C. for 2 h, the mixture was quenched with water and extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (2.47 g).

Workup

customthe mixture was quenched with water
extractionextracted with AcOEt
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record: ord-c8087302b1f44c80af4ed5eeb2214e86
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029536B2

Reaction notes

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