Reaction equation
C(O[C:6](=O)[NH:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10](Cl)[C:9]=1[CH:15]=O)(C)(C)C.[CH3:18][O-].[Na+]>>[N:7]1[C:8]2[C:9](=[CH:10][N:11]=[CH:12][CH:13]=2)[CH:15]=[CH:18][CH:6]=1Participants
3
Procedure
Reaction Scheme X illustrates an alternative preparation of the 1,6-naphthyridin-5(6H)-one compounds. In this Scheme, Weinreb amide VIII-2 is reacted with an aryl lithium reagent, generated from aryl bromide X-1, in which R is a protected or masked amino methyl derivative such as 1-(1-azido-1-methylethyl), to give ketone X-2. Condensation of this ketone with tert-butyl(2-chloro-3-formylpyridin-4-yl)carbamate in the presence of sodium methoxide, gives the 1,6-naphthyridine X-3. Deprotection or unmasking of the amine, in this case by palladium catalyzed reduction with hydrogen provides amine X-4. Treatment of X-4 with hydrochloric acid gives 1,6-naphthyridin-5(6H)-one X-5.
Sources & evidence
- ORD record
- ord-884254887e8c4f3497504859f3c301f1
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589068B2
Linked notes
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