2-Bromo-3-methylpyrazine

A solution of C39 (2.35 g, 5.78 mmol), 4-[3-Methyl-4-(4, 4, 5, 5-tetramethyl-1 , 3 , 2-dioxaborolan-2-yl)phenoxy]furo[3 , 2-c]pyridine (C2) (250 mg, 0.712 mmol), 5-bromo-4, 6-dimethylpyrimidine (160 mg, 0.855 mmcl), tris(dibenzylideneacetone)dipalladium(0) (95%, 26.9 mg, 0.142 mmol), tricyclohexyiphosphine (79.9 mg, 0.285 mmcl) and potassium phosphate (302 mg, 1.42 mmol) were combined in a 3:1mixture of 1 , 4-dioxane and water (12 mL), and subjected to irradiation in a microwave reactor at120 00 for 5 hours. The reaction mixture was filtered through Celite; the filtrate was concentrated under reduced pressure, taken up in ethyl acetate, filtered through silica gel (1 g), and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) afforded the product as a colorless oil. Yield: 123 mg, 0.371 mmol, 52%. LCMS m/z 332.1 (M+H). 1H NMR (500 MHz, ODd3) oe 8.98 (s, 1H), 8.07 (d, J5.9 Hz, 1H), 7.67 (d, J=2.2 Hz, 1H), 7.25-7.27 (m, 1H, assumed; partially obscured by solvent peak), 7.24(br d, J=2.4 Hz, 1H), 7.19 (brdd, J=8.3, 2.4 Hz, 1H), 7.08 (d, J=8.3 Hz, 1H), 6.90 (dd, J=2.2, 1.0 Hz, 1H), 2.27 (s, 6H), 2.04 (s, 3H).2-Bromo-3-methylpyrazine (104 mg, 0.600 mmol), tetrakis(triphenylphosphine)palladium(0) (95%, 133 mg, 0.109 mmol) and sodium carbonate(175 mg, 1.64 mmol) were combined with 4-[3-methoxy-4-(4, 4, 5, 5-tetramethyl-1 3, 2-dioxaborolan-2-yl)phenoxy]furo[3 , 2-c]pyridine [Cl 0, which was prepared in analogous fashion to4-[3-methyl-4-(4 , 4, 5, 5-tetramethyl-1 , 3 , 2-dioxaborolan-2-yl)phenoxy]furo[3, 2-c]pyrid me (C2) inExample 1] (200 mg, 0.545 mmol) in 1, 4-dioxane (3 mL) and water (1 mL). The reaction mixturewas heated to 13000 in a microwave reactor for 1 hour. The mixture was cooled to roomtemperature, and the supernatant was decanted into another flask. The remaining solids were washed with ethyl acetate (3 x 10 mL) and the combined organic portions were concentrated in vacuo. Purification was carried out twice using silica gel chromatography (First column: Eluent:2% methanol in dichloromethane; Second column: Gradient: 0% to 100% ethyl acetate inheptane). The colorless fractions were combined and concentrated under reduced pressure to provide the product as a white solid. Yield: 85 mg, 0.25 mmol, 46%. LCMS m/z 334.0 (M+H). 1H NMR (400 MHz, CDCl3) oe 8.47 (AB quartet, downfield doublet is broadened, JAB=2.S Hz, AVAB=l4 Hz, 2H), 8.08 (d, J=5.9 Hz, 1H), 7.66 (d, J=2.3 Hz, 1H), 7.36 (d, J8.0 Hz, 1H), 7.25- 7.28 (m, 1H, assumed; partially obscured by solvent peak), 6.90-6.96 (m, 2H), 6.88 (dd, J=2.2, 0.8 Hz, 1H), 3.79 (s, 3H), 2.50 (s, 3H). Yellow fractions were repurified to provide additional product: 55 mg, overall yield: 75%.EXAMPLE 10 A mixture of 8.56 parts of

Molecular Weight:173.01
XLogP3:1.2
Hydrogen Bond Acceptor Count:2
Exact Mass:171.96361
Monoisotopic Mass:171.96361
Topological Polar Surface Area:25.8
Heavy Atom Count:8
Complexity:76.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes