Methyl iodide → 2-methyl-2,6-naphthyridin-1(2H)-one
Reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[CH3:12]I>>[CH3:12][N:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[N:7][CH:6]=2)[C:1]1=[O:11]Participants
3
Procedure
A method for preparing compounds of Formula (III) is provided in Scheme 6. 2,6-Naphthyridin-1-ol (6-1) is subjected to alkylation with methyl iodide under basic conditions to provide 2-methyl-2,6-naphthyridin-1(2H)-one (6-2). Chlorination of 6-2 with N-chlorosuccinimide provides chloro compound 6-3. Treatment of 6-3 under palladium-catalyzed cross coupling conditions with a suitable halide provides compound 6-4. Selective reduction of the 2,6-naphthyridinone derivative provides the 5,6,7,8-tetrahydro-2,6-naphthyridin-1(2H)-one derivative 6-5.
Workup
- customis provided in Scheme 6
Sources & evidence
- ORD record
- ord-cc59f44dfbcb4aca98667c32b55cd4a5
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034900B2
Reaction notes
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