Diisopropylethylamine → HCID 86726788, compound

Temperature

100 °C

A solution of (2,6-difluorophenyl)boronic acid (270 mg, 1.7 mmol), methyl 3-amino-6-bromopyrazine-2-carboxylate (from Ark Pharm, 250 mg, 1.1 mmol), bis(tri-tert-butylphosphine) palladium (82 mg, 0.16 mmol), and DIPEA (370 μL, 2.1 mmol) in 1,4-dioxane (4 mL) and water (320 μL) in a vial was deoxygenated and purged with nitrogen several times. The vial was sealed and the reaction mixture was heated at 100° C. in the sealed vial for 14 h. The crude reaction mixture was filtered through a pad of diatomaceous earth and the inorganics were washed thoroughly with EtOAc. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography (40 g silica gel column, eluting with 0-50% EtOAc in hexanes) to afford the sub-title compound (258 mg, 91% yield). LC/MS (ESI) calc. for C12H10F2N3O2(M+H)+: m/z=266.1. found: 266.0.

1. custompurged with nitrogen several times
2. customThe vial was sealed
3. customThe crude reaction mixture
4. filtrationwas filtered through a pad of diatomaceous earth
5. washthe inorganics were washed thoroughly with EtOAc
6. concentrationThe filtrate was concentrated under reduced pressure
7. customthe residue was purified by flash chromatography (40 g silica gel column, eluting with 0-50% EtOAc in hexanes)

ORD record

ord-927f8bafdb854887924b2a9886e1f724

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09200004B2