1-Propanol → HCID 86642063, compound

Temperature

0 °C

To a solution of DIPA (15.5 mL) in THF (300 mL), cooled to −78° C., was added n-BuLi (2.35N in hexanes, 44 mL). The reaction mixture was stirred 5 min at this temperature before warming to 0° C. The reaction mixture was stirred 15 min before cooling to −78° C. 3-fluoro-6-methoxy-quinoline (prepared as described in FR 2004/01105, 15 g) in THF (50 mL+10 mL rinse) was added and the mixture was stirred 3 h at −78° C. DMF (3 mL) was added quickly. After 45 min., 1-propanol (8 mL) was added and the mixture was warmed to rt. The mixture was partitioned between water (100 mL) and EA (200 mL). The aq. layer was extracted with EA (200 mL). The combined org. layers were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue triturated in Hept to give an orange solid (9.0 g, 51% yield).

1. stirringThe reaction mixture was stirred 15 min
2. temperaturebefore cooling to −78° C
3. stirringthe mixture was stirred 3 h at −78° C
4. waitAfter 45 min.
5. temperaturethe mixture was warmed to rt
6. customThe mixture was partitioned between water (100 mL) and EA (200 mL)
7. extractionThe aq. layer was extracted with EA (200 mL)
8. washlayers were washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated to dryness
12. customThe residue triturated in Hept

ORD record

ord-b88e9cdc528f463283c88b61a42a56c7

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193179B2