1,1'-Carbonyldiimidazole → HCID 67189327, compound

To a stirred solution of 5-bromo-2-(2-chlorophenylamino)benzonitrile (0.8201 g, 2.67 mmol) in THF (10.00 ml, 2.67 mmol) was slowly added borane-THF (10.7 ml, 10.7 mmol) at RT for 10 min and the resulting mixture was stirred continuously over night. The mixture was quenched with slow addition of MeOH until all bubbling subsided. The mixture was concentrated in vacco. The residue was diluted with NaHCO3(aq) and water (5 mL each) and the separated aqueous layer was extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to give the crude residue, which was taken up in THF (8.00 ml) and treated with di(1H-imidazol-1-yl)methanone (0.519 g, 3.20 mmol) at RT. After stirring for 30 min, to the mixture was added potassium 2-methylpropan-2-olate (0.748 g, 6.67 mmol). The suspension was stirred at RT for 1 h and washed with EtOAc-ether to give 6-bromo-1-(2-chlorophenyl)-3,4-dihydroquinazolin-2(1H)-one as a white solid. MS m/e 336 (M+H)+.

1. customat RT
2. customfor 10 min
3. customThe mixture was quenched with slow addition of MeOH until all bubbling
4. concentrationThe mixture was concentrated in vacco
5. additionThe residue was diluted with NaHCO3(aq) and water (5 mL each)
6. extractionthe separated aqueous layer was extracted with EtOAc (3×10 mL)
7. washThe combined organic layers were washed with brine
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated
10. customto give the crude residue, which
11. stirringAfter stirring for 30 min, to the mixture
12. stirringThe suspension was stirred at RT for 1 h
13. washwashed with EtOAc-ether

ORD record

ord-ff0ffa860f52421190052676a29db2c7

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935709B2