Hydrochloric Acid → HCID 67055974, compound

Temperature

125 °C

A microwave vial was charged with 3,5-dibromo pyridine (5.00 g, 21.1 mmol), Pd(OAc)2, (0.185 g, 0.820 mmol), 1,3-Bis(diphenylphosphino)propane (0.7 g 1.7 mmol), and 1-butyl-3-methylimidazolium tetrafluoroborate (25 mL) under nitrogen at room temperature. The reaction mixture was degassed three times and allyl alcohol (2.85 g, 49.1 mmol) and triethylamine (4.7 ml, 3.6 mmol) were added. The reaction mixture was heated in microwave reactor at 125° C. for 2 h. After cooling to room temperature, aqueous HCl (20 mL, 10%) was added and the mixture stirred for 1 h. The reaction mixture was treated with saturated Na2CO3 (20 mL) and the aqueous portion extracted with CH2Cl2. The combined organic layers were washed with water and brine, dried with Na2SO4 and evaporated under reduced pressure. The resulting residue was purified by flash silica gel chromatography (SiO2, hexane/EtOAc=8/2) to yield 2-(5-bromopyridin-3-yl)prop-2-en-1-ol (1.6 g, 36%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.69 (d, 1H, J=2 Hz), 8.62 (d, 1H, J=2.4 Hz), 8.13 (s, 1H), 5.66 (s, 1H), 5.45 (s, 1H), 5.15 (t, 1H, J=5.2 Hz), 4.35 (d, 2H, J=5.2 Hz). LCMS Method T: retention time 0.96 min; [M+1]=216.

1. additionwere added
2. temperatureAfter cooling to room temperature
3. extractionthe aqueous portion extracted with CH2Cl2
4. washThe combined organic layers were washed with water and brine
5. dry with materialdried with Na2SO4
6. customevaporated under reduced pressure
7. customThe resulting residue was purified by flash silica gel chromatography (SiO2, hexane/EtOAc=8/2)

ORD record

ord-3c10a766c12a4135ac0f7626076fb623

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575184B2