Sodium Carbonate → 5-Bromo-3-(4-fluorophenyl)pyrazin-2-amine

HRID 1865873Notes

Reaction equation

Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:8][C:6]1[N:7]=[C:2]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)[C:3]([NH2:9])=[N:4][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5.058 g of 3,5-dibromo-pyrazin-2-ylamine in 100.0 ml 1,2-dimethoxyethane was added at room temperature 1.156 g of tetrakis(triphenylphosphine) palladium (0) and stirred for 0.5 hours. To the resulting mixture was added a solution of 5.30 g sodium carbonate in 50.0 ml water and 3.078 g 4-fluorophenylboronic acid. The mixture was heated to 100° C. for 5 h. The resulting yellow solution was partitioned between 10% aqueous citric acid and ethyl acetate. The organic layer washed with 10% aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel with a gradient of heptane to dichloromethane to yield 3.22 g of the title compound as white crystals. MS (ISP) (M+H+)=268.1 and 270.1

Workup

customThe resulting yellow solution was partitioned between 10% aqueous citric acid and ethyl acetate
washThe organic layer washed with 10% aqueous sodium bicarbonate and brine
dry with materialdried over magnesium sulfate
customevaporated
customThe residue was purified by chromatography on silica gel with a gradient of heptane to dichloromethane

Sources & evidence

ORD record: ord-a719aaabe79a47f5811f1517a636e559
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629346B2

Reaction notes

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