Quinoline → HCID 86594125, compound
Reaction equation
N1C2C(=CC=CC=2)C=CC=1.[C:11](=[C:13]1[CH2:22][C:21](=O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14]1)=[O:12].[F:24][C:25]([F:38])([F:37])[S:26]([O:29]S(C(F)(F)F)(=O)=O)(=[O:28])=[O:27]>>[F:24][C:25]([F:38])([F:37])[S:26]([O:29][N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]1=[C:11]=[O:12])(=[O:28])=[O:27]Participants
Conditions
- Temperature
- 0 °C
Procedure
Compounds of Formula I in which ring A is a quinoline can be prepared from a carbonyl-quinolin-1-one (XLM) via the method depicted in Scheme IXb. The carbonyl-quinolin-4-one (XLI) is converted to a triflate group by adding about 1.1 eq. to about 1.5 eq. trifluoromethanesulfonic anhydride (Tf2O) to a basic solution of the carbonyl-quinolin-1-one (XLIII) which is maintained at about 0° C. The reaction is complete in about 1 h to about 3 h to form a 1-trifluoromethanesulfonyloxy-carbonyl-quinoline (LXX). The triflate group can be reacted with a substituted phenylboronic acid (X) via the method depicted in Scheme I to form a (substituted phenyl)-carbonyl-quinoline (LXXI). The carbonyl group of the (substituted phenyl)-carbonyl-quinoline (LXXI) can be converted to an α,β-unsaturated carboxylic ester by adding the (substituted phenyl)-carbonyl-quinoline (LXXI) to a solution of 2-lithio-1,1-diflouroethene (prepared by combining an alkyl lithium with 1,1-difluoroethene at about −78° C.) while maintaining a temperature below −78° C. The resulting alcohol is isolated and immediately treated with methanol and H2SO4 to give a compound of Formula I in which ring A is a quinoline (LXXII).
Workup
- waitThe reaction is complete in about 1 h to about 3 h
Sources & evidence
- ORD record
- ord-54403f1f9cdd468fa52b54fe9c683f2e
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07348359B2
Reaction notes
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