Water → 5-(6-chloro-3-methylpyridin-2-yl)-1-methyl-1H-indazole

Temperature

110 °C

In a 10 mL reaction vial, the 1-methyl-1H-indazol-5-ylboronic acid (500 mg, 2.84 mmol) and the 2-bromo-6-chloro-3-methylpyridine (585 mg, 2.84 mmol) were dissolved in dioxane (7 mL) and water (1.7 mL) under argon atmosphere. The mixture was bubbled with argon for 5 min. Then potassium carbonate (979 mg, 7.1 mmol) and Pd(PPh3)4 (49 3 mg, 0.428 mmol) were added sequentially. The resulting reaction mixture was then sealed and heated in oil bath at 110° C. for 2.5 h. Reaction was then partitioned between EtOAc (30 mL) and water (30 mL).The organic phase was washed with water (3×20 mL) and was concentrated. Residue was purified on silica gel column with 0-50% EtOAc/Hex to afford the title compound. LCMS-ESI+: calc'd for: C14H12ClN3: 258.1 and 260.1 (M+H+); found: 258.0 and 260.0 (M+H+).

1. customIn a 10 mL reaction vial
2. customThe mixture was bubbled with argon for 5 min
3. customThe resulting reaction mixture
4. customwas then sealed
5. customReaction
6. customwas then partitioned between EtOAc (30 mL) and water (30 mL).The organic phase
7. washwas washed with water (3×20 mL)
8. concentrationwas concentrated
9. customResidue was purified on silica gel column with 0-50% EtOAc/Hex

ORD record

ord-b5c872eeb1ad4bcfadee83c0d521edbd

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987250B2