Potassium Phosphate, Tribasic → 2-[6-(1,2-Dimethyl-1h-imidazol-5-yl)-2,3-dihydro-4h-1,4-benzoxazin-4-yl]-6,6-dimethyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

Temperature

140 °C

To a solution of Example 292 (75 mg, 0.17 mmol) in THF (3 mL) and water (1 mL) was added tetra-n-butylammonium bromide (107 mg, 0.34 mmol), potassium phosphate (72 mg, 0.34 mmol), 5-bromo-1,2-dimethyl-1H-imidazole (60 mg, 0.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol). The reaction was heated at 140° C. under microwave irradiation for 25 minutes. The resulting mixture was partitioned between DCM (50 mL) and water (50 mL); the organic fraction was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo. The residue was purified by preparative HPLC (Method 7) to yield the title compound (20 mg, 28%) as a white solid. δH (CDCl3) 7.99 (1H, d, J 1.9 Hz), 7.06 (1H, dd, J 8.5 and 1.9 Hz), 7.01 (1H, d, J 8.5 Hz), 6.93 (1H, s), 5.34 (1H, s), 4.40-4.35 (2H, m), 4.19-4.13 (2H, m), 3.57 (3H, s), 2.87 (2H, s), 2.46 (3H, s), 1.40 (6H, s). LCMS (ES+) 410.0 (M+H)+, RT 1.95 minutes (Method 1).

1. customThe resulting mixture was partitioned between DCM (50 mL) and water (50 mL)
2. washthe organic fraction was washed with brine (50 mL)
3. dry with materialdried (MgSO4)
4. concentrationconcentrated in vacuo
5. customThe residue was purified by preparative HPLC (Method 7)

ORD record

ord-bed36c4dd07149bbbbf8d2756c5008e7

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242116B2