Triethylamine → HCID 59165834, compound

To a solution of 6-bromopyridin-2-amine (660 mg, 3.8 mmol) and Et3N (1.1 mL, 7.7 mmol) in dichloromethane (5 mL) was added a solution of 1-(2,2-difluorobenzo-[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (1.0 g, 3.8 mmol) in dichloromethane (5 mL). The resulting reaction mixture was allowed to stir at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane (5 mL) and was washed with 1 N aqueous HCl (1×10 mL) and saturated aqueous NaHCO3 (1×10 mL). The organics were dried over sodium sulfate and evaporated to dryness. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-70% ethyl acetate in hexane to yield N-(6-bromopyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (780 mg, 51%). 1H NMR (400 MHz, DMSO-d6) δ 9.46 (s, 1H), 8.01-7.99 (m, 1H), 7.75-7.71 (m, 1H), 7.54 (m, 1H), 7.41-7.39 (m, 1H), 7.36-7.30 (m, 2H), 1.52-1.49 (m, 2H), 1.20-1.17 (m, 2H).

1. customThe resulting reaction mixture
2. washwas washed with 1 N aqueous HCl (1×10 mL) and saturated aqueous NaHCO3 (1×10 mL)
3. dry with materialThe organics were dried over sodium sulfate
4. customevaporated to dryness
5. customThe resulting residue was purified by silica gel chromatography
6. washeluting with a gradient of 0-70% ethyl acetate in hexane

ORD record

ord-4cb73744b6704c8d9baf72b0f492f866

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07659268B2