Triethylamine → HCID 22060166, compound

Temperature

131 °C

A mixture of 2-amino-5-bromo-3-methylpyridine (1.41 g, 7.53 mmol), N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine (1.50 g, 7.53 mmol), palladium(II) acetate (33.8 mg, 0.15 mmol), tri-o-tolylphosphine (183.2 mg, 0.60 mmol), triethylamine (4.50 mL, 32.3 mmol), and anhydrous acetonitrile (8 mL) was stirred and heated at 130-132° C. in a sealed glass tube for 18 h. The mixture was further heated at 140° C. for 84 h. The resulting dark-brown solution was cooled to ambient temperature and concentrated by rotary evaporation. The residue was diluted with water (25 mL) and extracted with CH2Cl2 (3×25 mL). The combined CH2Cl2 extracts were dried (Na2SO4), filtered, concentrated by rotary evaporation, and vacuum dried producing a dark-brown oil (2.84 g). The crude product was purified by column chromatography on silica gel (135 g), eluting with ethyl acetate-hexane (3:1, v/v) to remove impurities, followed by elution with CH3OH-Et3N (98:2, v/v) to collect the product. Fractions containing the product (Rf 0.70) were combined and dissolved in CHCl3. The CHCl3 solution was dried (Na2SO4), filtered, concentrated by rotary evaporation, and vacuum dried to give 1.11 g (48.4%) of an amber-brown oil.

1. temperatureThe mixture was further heated at 140° C. for 84 h
2. temperatureThe resulting dark-brown solution was cooled to ambient temperature
3. concentrationconcentrated by rotary evaporation
4. additionThe residue was diluted with water (25 mL)
5. extractionextracted with CH2Cl2 (3×25 mL)
6. dry with materialThe combined CH2Cl2 extracts were dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated by rotary evaporation, and vacuum
9. customdried

ORD record

ord-5e2115d4191c47c7bfa43b2b7b3051fd

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288420B2