Sodium Carbonate → 4-(3-Chloropyrazin-2-yl)-1-naphthonitrile

HRID 45780

Reaction equation

Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([C:27]#[N:28])=[CH:19][CH:18]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[Cl:8][C:7]1[C:2]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([C:27]#[N:28])=[CH:19][CH:18]=2)=[N:3][CH:4]=[CH:5][N:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2,3-dichloropyrazine (2.98 g, 2 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthonitrile (0.558 mmol, 2 mmol) palladium tetrakis triphenylphoshine (0.069 g, 0.06 mmol) and aqueous sodium carbonate solution (2M, 3 mL, 6 mmol) in dioxane (7 mL) was heated to 80° C. for 12 hours. The reaction mixture cooled to room temperature, washed with water, extracted with ethyl acetate and purified by chromatography to yield 4-(3-chloropyrazin-2-yl)-1-naphthonitrile (0.36 g, 68%).

Workup

temperatureThe reaction mixture cooled to room temperature
washwashed with water
extractionextracted with ethyl acetate
custompurified by chromatography

Sources & evidence

ORD record: ord-c8158e5459884ad6907ccb259ea092f2
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541589B2

Linked notes

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