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). ESI-MS m/z calc. 396.0. found 397.3 (M+1)+. Retention time 2.12 minutes.

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-13f4bbfa24f54974abe65a8909dd1549

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324207B2