Triethylamine → 4-(5-Bromopyridin-2-yl)-1,4-diazepan-2-one

A solution of 3-bromo-6-fluoropyridine (315 mg, 1.79 mmol), 1,4-diazepan-2-one (200 mg, 1.75 mmol), and triethylamine (0.269 ml, 1.93 mmol) in N,N-dimethylacetamide (3 mL) was irradiated in a microwave reactor for twenty minutes at 220° C. The reaction mixture was diluted with ethyl acetate (35 mL) and then washed with saturated aqueous sodium bicarbonate (15 mL), water (3×10 mL), and brine (15 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0.5-8.5% methanol/dichloromethane) to afford 4-(5-bromopyridin-2-yl)-1,4-diazepan-2-one. MS ESI calc'd. for C10H13BrN3O [M+H]+ 270 and 272. found 270 and 272. 1H NMR (500 MHz, DMSO-d6): δ 8.14 (d, J=2.4 Hz, 1H), 7.68 (dd, J=9.1, 2.7 Hz, 1H), 7.48 (m, 1H), 6.70 (d, J=9.1 Hz, 1H), 4.11 (s, 2H), 3.85 (s, 2H), 3.18 (m, 2H), 1.62 (m, 2H).

1. washwashed with saturated aqueous sodium bicarbonate (15 mL), water (3×10 mL), and brine (15 mL)
2. dry with materialThe organic layer was dried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by chromatography on silica gel (0.5-8.5% methanol/dichloromethane)

ORD-Eintrag

ord-826abac64754418ab8373702dfe5b108

Quelldatensatz

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09376418B2