Potassium Carbonate → 8-chloro-9-methoxy-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one

HRID 1398385Notes

Reaction equation

Br[C:2]1[C:18]([Cl:19])=[CH:17][C:5]2[N:6]([CH3:16])[C:7](=[O:15])[C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[N:10][C:9]=3[CH3:14].N1CCC[C@H]1[C:22](O)=[O:23].C[O-].[Na+].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.CO.[Cu]I>[Cl:19][C:18]1[C:2]([O:23][CH3:22])=[CH:3][C:4]2[C:13]3[C:8](=[C:9]([CH3:14])[N:10]=[CH:11][CH:12]=3)[C:7](=[O:15])[N:6]([CH3:16])[C:5]=2[CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 9-bromo-8-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (0.05 g, 0.148 mmol), copper(I)iodide (0.031 g, 0.163 mmol), L-proline (0.020 g, 0.178 mmol), sodium methoxide (0.040 g, 0.741 mmol) and K2CO3 (0.041 g, 0.296 mmol) were stirred in DMSO (1.5 mL). The mixture was heated to 80° C. for 16 h. After cooling, the crude reaction mixture was diluted with methanol, filtered through diatomaceous earth (Celite®) and concentrated under reduced pressure to afford 8-chloro-9-methoxy-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one, as brown solid (40 mg). LC/MS (ESI) m/e 289.0 [(M)+, calcd for C15H14ClN2O2, 289.1]; LC/MS retention time (method D): tR=0.89 min.

Workup

temperatureAfter cooling
customthe crude reaction mixture
filtrationfiltered through diatomaceous earth (Celite®)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f30ab96e7ec349d8b2c904b378d9a0a1
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901305B2

Reaction notes

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