US 7,598,380 B2
Method of preparation of azaindole derivatives
Wansheng Liu, Edison, N.J. (US); Sunil S. Patel, Edison, N.J. (US); Nicolas Cuniere, Belle Mead, N.J. (US); Yvonne Lear, Candiac (Canada); Prashant P. Deshpande, Princeton, N.J. (US); Jeffrey N. Simon, Lawrenceville, N.J. (US); Chiajen Lai, Kendall Park, N.J. (US); Annie J. Pullockaran, Pennington, N.J. (US); Nachimuthu Soundararajan, Kendall Park, N.J. (US); and Jeffrey T. Bien, Princeton, N.J. (US)
Assigned to Bristol-Myers Squibb Company, Princeton, N.J. (US)
Filed on Jul. 25, 2006, as Appl. No. 11/492,750.
Claims priority of provisional application 60/705230, filed on Aug. 03, 2005.
Prior Publication US 2007/0032503 A1, Feb. 08, 2007
Int. Cl. C07D 487/04 (2006.01); C07D 213/69 (2006.01); C07D 213/73 (2006.01)
U.S. Cl. 544—362  [546/296; 546/311] 15 Claims
 
1. A method of preparing a compound of formula 8:

OG Complex Work Unit Drawing
comprising the steps of:
(a) converting a compound of formula 1:

OG Complex Work Unit Drawing
to a compound of formula 2:

OG Complex Work Unit Drawing
(b) converting said compound of formula 2 to a compound of formula 3:

OG Complex Work Unit Drawing
(c) converting said compound of formula 3 to a compound of formula 4:

OG Complex Work Unit Drawing
(d) converting said compound of formula 4 to a compound of formula 5:

OG Complex Work Unit Drawing
(e) cyclizing said compound of formula 5 to a compound of formula 6:

OG Complex Work Unit Drawing
(f) converting said compound of formula 6 to a compound of formula 7:

OG Complex Work Unit Drawing
and
(g) coupling said compound of formula 7 with a compound of formula 9:

OG Complex Work Unit Drawing