Potassium Phosphate, Tribasic → 2-[6-(1-Benzothien-2-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

A stirred solution of Example 292 (0.048 g, 0.109 mmol), 2-bromobenzothiophene (0.035 g, 0.163 mmol), potassium phosphate (0.045 g, 0.212 mmol), tetra-n-butyl-ammonium bromide (0.045 g, 0.140 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.008 g, 0.007 mmol) in THF (2 mL) and H2O (0.5 mL) was heated to 100° C. in a sealed vessel under a nitrogen atmosphere for 1 h. The reaction mixture was diluted with DCM (10 mL) and washed with water (10 mL) and brine (10 mL). The organic fraction was dried (MgSO4) and concentrated in vacuo. Purification by preparative HPLC (Method 6) gave the title compound (0.003 g, 7%) as a white solid. δH (CDCl3) 8.35 (1H, d, J 2.1 Hz), 7.88-7.73 (2H, m), 7.46 (1H, s), 7.41 (1H, dd, J 8.5 and 2.1 Hz), 7.37-7.28 (2H, m), 7.01 (1H, d, J 8.5 Hz), 5.27 (1H, s), 4.42-4.35 (2H, m), 4.23-4.17 (2H, m), 2.91 (2H, s), 1.42 (6H, s). LCMS (ES+) 448 (M+H)+, RT 4.37 minutes (Method 1).

1. washwashed with water (10 mL) and brine (10 mL)
2. dry with materialThe organic fraction was dried (MgSO4)
3. concentrationconcentrated in vacuo
4. customPurification by preparative HPLC (Method 6)

ORD-Eintrag

ord-2ee45f7cf75647b990a03ba54dab1e8b

Quelldatensatz

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08242116B2