反应详情

温度

100 °C

A stirred suspension of 9-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide (0.70 g; 2.2 mmol) and dimethylformamide dimethylacetal (DMF·DMA, 6 ml) in toluene (5 ml) was heated at 100° C. overnight (16 h) upon which time the reaction mixture was concentrated. To the resulting residue was added AcOH (5 ml), water (0.5 ml) and 2,4-difluorophenylhydrazine hydrochloride (0.56 g; 3.1 mmol) and the resulting solution heated at 100° C. for 3 h. The reaction mixture was concentrated, the residue was dissolved in CH2Cl2 (50 ml) and washed with satd. NaHCO3 (50 ml). The organic layer was separated (hydrophobic frit), concentrated and purified by ISCO to give 399 as a cream-coloured solid (0.31 g; 31%). δH (400 MHz, CDCl3) 3.41 (t, J=5.2, 2H), 4.36 (t, J=5.2, 2H), 6.89 (d, J=8.8, 1H), 7.14-7.20 (m, 2H), 7.27-7.30 (m, 1H), 7.55-7.61 (m, 1H), 7.69 (d, J=2.8, 1H), 8.16 (s, 1H). [M+H]+: 462

1. concentrationwas concentrated
2. temperaturethe resulting solution heated at 100° C. for 3 h
3. concentrationThe reaction mixture was concentrated
4. dissolutionthe residue was dissolved in CH2Cl2 (50 ml)
5. washwashed with satd
6. customThe organic layer was separated (hydrophobic frit)
7. concentrationconcentrated
8. custompurified by ISCO