Pyridine → HCID 59305329, compound

To a stirred solution of 3-(5-Bromo-2-fluoro-phenyl)-propan-1-ol (0.53 g, 2.3 mmol) in dry methylene chloride (10 mL) at 0° C. and under a nitrogen atmosphere was added pyridine (0.46 mL, 5.6 mmol) and tosyl chloride (0.47, 2.5 mmol). The cooling bath was removed and the mixture was warmed to room temperature for 12 h, and then quenched with 2 N HCl (6 mL). The mixture was partitioned between methylene chloride and H2O, and the aqueous layer was extracted with methylene chloride (2×10 mL). The organic layer was washed with brine and dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography (10-20% Ethyl acetate/Petroleum Ether) to afford the titled compound (0.6 g, 69%) as a clear oil, identified by NMR and mass spectral analyses; MS (ES+): 403 (M+NH4+).

1. customThe cooling bath was removed
2. customquenched with 2 N HCl (6 mL)
3. customThe mixture was partitioned between methylene chloride and H2O
4. extractionthe aqueous layer was extracted with methylene chloride (2×10 mL)
5. washThe organic layer was washed with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude material was purified by silica gel chromatography (10-20% Ethyl acetate/Petroleum Ether)

ORD record

ord-7d8319aafa194bc698c177bb8d87382e

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07723368B2