Water → 8-amino-4-(3-bromophenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one

Temperature

90 °C

To a stirred solution of compound 3 (0.1 g, 0.27 mmol) in EtOH:H2O (10 mL, 6:3) was added Fe-powder (0.076 g, 1.39 mmol) followed by NH4Cl (0.037 g, 0.70 mmol) at RT. The resulting reaction mixture was heated to 90° C. and stirred for 1 h; progress of the reaction was monitored by TLC. The reaction mixture was then cooled to RT; the reaction mixture was filtered and the obtained filtrate was concentrated under reduced pressure. The residue was diluted with water (10 mL) and then extracted with EtOAc (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 4 (35 mg, 38%) as yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.32 (bs, 1H), 8.15-8.13 (m, 1H), 7.97 (d, J=7.6 Hz, 1H), 7.69 (d, J=7.2 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.12 (d, J=8.8 Hz, 1H), 6.52 (d, J=8.4 Hz, 1H), 6.32 (s, 1H), 5.48 (bs, 2H), 3.42 (s, 2H). Mass: m/z 331 [M+1]+

1. customThe resulting reaction mixture
2. temperatureThe reaction mixture was then cooled to RT
3. filtrationthe reaction mixture was filtered
4. concentrationthe obtained filtrate was concentrated under reduced pressure
5. additionThe residue was diluted with water (10 mL)
6. extractionextracted with EtOAc (2×10 mL)
7. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
8. concentrationconcentrated under reduced pressure

ORD record

ord-fdca6cccf84947098ccc73eb707c0467

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193710B2