Dimethylformamide → HCID 86642063, compound

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 (15 g, 84.7 mmol; see WO 2006/058700) in THF (50 mL+10 mL rinse) was added and the mixture was stirred 3 h at −78° C. DMF (3 mL, 1.2 eq.) was added quickly (within one min). After 45 min, the reaction mixture was quenched by adding 1-propanol (8 mL). The mixture was warmed to rt and extracted twice with EA. The combined org. layers were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue triturated in Hept to give the title intermediate as an orange solid (9.0 g, 52% 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. customthe reaction mixture was quenched
6. additionby adding 1-propanol (8 mL)
7. temperatureThe mixture was warmed to rt
8. extractionextracted twice with EA
9. washlayers were washed with brine
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated to dryness
13. customThe residue triturated in Hept

ORD record

ord-fd3b299ed96a436abdfee15513ee4185

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08114867B2