tert-butyl 4-(quinolin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate → HCID 19096226, compound

A catalytic amount of 50% wet 10% palladium on carbon was added to a mixture of tert-butyl 4-(quinolin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (260 mg, 0.84 mmol) in methanol (10 mL). Reaction vessel was placed on a Parr apparatus and charged with 10 psi of hydrogen gas. Reaction shook at room temperature for 4 hours. Mixture was filtered to removed catalyst. Filtrate was concentrated in vacuo. Residue was dissolved in dichloromethane (4 mL). Trifluoroacetic acid (1 mL) was added to the mixture. Reaction stirred at room temperature for 2 hours. Reaction mixture was concentrated in vacuo. Residue was dissolved in dichloromethane (20 mL). Mixture was washed with aqueous sodium bicarbonate (20 mL). Aqueous layer was back extracted with dichloromethane (30 mL). Organic layers were combined, dried (magnesium sulfate), filtered and concentrated in vacuo. Title compound was obtained as yellow oil in 45% yield. MS m/e (M+H)+=213.2.

1. customReaction vessel
2. customReaction
3. filtrationMixture was filtered
4. customto removed catalyst
5. concentrationFiltrate was concentrated in vacuo
6. dissolutionResidue was dissolved in dichloromethane (4 mL)
7. additionTrifluoroacetic acid (1 mL) was added to the mixture
8. customReaction
9. stirringstirred at room temperature for 2 hours
10. customReaction mixture
11. concentrationwas concentrated in vacuo
12. dissolutionResidue was dissolved in dichloromethane (20 mL)
13. washMixture was washed with aqueous sodium bicarbonate (20 mL)
14. extractionAqueous layer was back extracted with dichloromethane (30 mL)
15. dry with materialdried (magnesium sulfate)
16. filtrationfiltered
17. concentrationconcentrated in vacuo

ORD record

ord-5ec022d12876407e8f7f29785c612288

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07384931B2