Water → tert-butyl 8-isobutoxy-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate

Temperature

70 °C

To a solution of isobutyl alcohol (0.16 mL) in toluene (4 mL) was added sodium hydride (0.14 g), and the resulting mixture was stirred at 70° C. for 15 min under a nitrogen atmosphere. A mixture of tert-butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.50 g), BINAP (0.033 g), Pd2(dba)3 (0.024 g) and toluene (4 mL) was added, and the resulting mixture was stirred at 100° C. for 2 hr under an argon atmosphere. The reaction solution was poured into water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane) to give tert-butyl 8-isobutoxy-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.33 g, 58%) as a yellow oil.

1. additionwas added
2. stirringthe resulting mixture was stirred at 100° C. for 2 hr under an argon atmosphere
3. extractionthe resulting product was extracted with ethyl acetate
4. washThe organic layer was washed with water and saturated brine
5. customdried
6. customthe solvent was evaporated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane)

ORD record

ord-020d6e24b5fd47b99e7247fa5492b884

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329687B2