Sodium hydride → HCID 86706318, compound

To a stirred solution of 6-bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 0.060 g, 0.217) in anhydrous DMF (0.8 mL) was added sodium hydride 60% (0.013 g, 7.8 mg, 0.325 mmol). The reaction mixture was stirred at room temperature for 5 minutes under argon, then a solution of 3-(bromomethyl)-5-methylisoxazole (0.057 g, 0.325 mmol) in anhydrous DMF (0.3 mL) was added. The stirring was continued at room temp for 1 hour and 50 minutes. The reaction mixture was diluted with ethyl acetate (40 mL) and the solution was washed with water (10 mL), brine (2×10 mL), dried (Na2SO4) and concentrated in vacuo. The residue was purified using preparative TLC eluting with 20% ethyl acetate in CH2Cl2. The product band was recovered and stirred with 5% MeOH in ethyl acetate. The silica was removed by filtration, washed with 5% MeOH in EtOAc (2×5 mL), acetone (2×8 mL). The title compound was obtained as an off-white solid (0.065 g, 80%). 1H-NMR (500 MHz, DMSO-d6) 2.31 (s, 3H), 3.89 (s, 3H), 5.58 (s, 2H), 5.89 (s, 1H), 6.75 (s, 1H), 7.78 (s, 1H), 7.83 (s, 1H), 8.12 (s, 1H), 8.57 (s, 1H).

1. waitThe stirring was continued at room temp for 1 hour and 50 minutes
2. washthe solution was washed with water (10 mL), brine (2×10 mL)
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated in vacuo
5. customThe residue was purified
6. washeluting with 20% ethyl acetate in CH2Cl2
7. customThe product band was recovered
8. stirringstirred with 5% MeOH in ethyl acetate
9. customThe silica was removed by filtration
10. washwashed with 5% MeOH in EtOAc (2×5 mL), acetone (2×8 mL)

ORD record

ord-af1ca3c493b8477ea6a26fa7b7204f69

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371319B2