tert-Butyl 4-bromo-3-cyano-5,6-dihydro-1,7-naphthyridine-7(8h)-carboxylate synthesis

4synthesis methods

Product Name:tert-Butyl 4-bromo-3-cyano-5,6-dihydro-1,7-naphthyridine-7(8h)-carboxylate
CAS Number:1333996-55-6
Molecular formula:C14H16BrN3O2
Molecular Weight:338.2

57597-62-3
107 suppliers
$40.00/1g

1-tert-butyl 4-ethyl 3-aMino-5,6-dihydropyridine-1,4(2H)-dicarboxylate

1005333-24-3
8 suppliers
inquiry

tert-Butyl 4-bromo-3-cyano-5,6-dihydro-1,7-naphthyridine-7(8h)-carboxylate

1333996-55-6
18 suppliers
inquiry

Yield:1333996-55-6 42%

Reaction Conditions:

Stage #1: 3,3-dimethoxypropionitrile;1-(tert-butyl) 4-ethyl 5-amino-3,6-dihydropyridine-1,4(2H)-dicarboxylatewith tert.-butyl lithium in tetrahydrofuran at 0 - 70; for 1.08333 h;Inert atmosphere;
Stage #2: with phosphorus tribromide in dichloromethane;N,N-dimethyl-formamide at 0; for 0.5 h;Inert atmosphere;

References:

Demont, Emmanuel H.;Arpino, Sandra;Bit, Rino A.;Campbell, Colin A.;Deeks, Nigel;Desai, Sapna;Dowell, Simon J.;Gaskin, Pam;Gray, James R. J.;Harrison, Lee A.;Haynes, Andrea;Heightman, Tom D.;Holmes, Duncan S.;Humphreys, Philip G.;Kumar, Umesh;Morse, Mary A.;Osborne, Greg J.;Panchal, Terry;Philpott, Karen L.;Taylor, Simon;Watson, Robert;Willis, Robert;Witherington, Jason [Journal of Medicinal Chemistry,2011,vol. 54,# 19,p. 6724 - 6733] Location in patent:supporting information; experimental part

24424-99-5 Synthesis

24424-99-5
825 suppliers
$13.50/25G

1333996-55-6
18 suppliers
inquiry

References

Ethyl N-benzyl-3-oxo-4-piperidine-carboxylate hydrochloride

52763-21-0
242 suppliers
$6.00/1g

1333996-55-6
18 suppliers
inquiry

References

206111-40-2 Synthesis

1-tert-butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate

206111-40-2
19 suppliers
inquiry

1333996-55-6
18 suppliers
inquiry

References