Cesium carbonate → (4-(3-Chloropyrazin-2-yloxy)phenyl)(pyridin-2-YL)methanone

HRID 473623Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:22][C:23]1[C:28](Cl)=[N:27][CH:26]=[CH:25][N:24]=1>CN(C=O)C>[Cl:22][C:23]1[C:28]([O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=3)=[O:9])=[CH:4][CH:3]=2)=[N:27][CH:26]=[CH:25][N:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of (4-hydroxy-phenyl)-pyridin-2-yl-methanone (2.5 g, 0.0125 mol) in DMF (35 mL) was added cesium carbonate (6.14 g, 0.0188 mol). The resulting mixture was stirred for 15 minutes before addition of 2,3-dichloro pyrazine(1.87 g, 0.0125 mol) at 0° C. The reaction mixture was heated to 80° C. for 16 h. The reaction mixture was partitioned between water (100 mL) and ethyl acetate (2×100 mL). The organic layer was dried over sodium sulphate and concentrated to afford the product. MS (ESI, pos. ion) m/z: 312 (M+1). IC50 (uM) 30.

Workup

customThe reaction mixture was partitioned between water (100 mL) and ethyl acetate (2×100 mL)
dry with materialThe organic layer was dried over sodium sulphate
concentrationconcentrated
customto afford the product

Sources & evidence

ORD record: ord-d737fc1266e849f08fe4a3fe155e347b
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637500B2

Reaction notes

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