Potassium Carbonate → HCID 58168016, compound

HRID 1029104Notes

Reaction equation

HRID 1029104 reaction equation
F[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.BrC1[CH:19]=[C:20]([CH:23]=CC=1)[CH2:21]O.C(=O)([O-])[O-:27].[K+].[K+]>CN(C=O)C.CO>[C:20]([O:27][C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3)([CH3:23])([CH3:21])[CH3:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 851413-Bromobenzyl alcoholHCID 58168117HCID 58168117, compound

Product 1

HCID 58168016HCID 58168016, compoundYield 3.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

9-Fluoro-5H-benzo[c][1,8]naphthyridin-6-one (40 mg, 0.19 mmol), 3-bromobenzyl alcohol (105 mg, 0.56 mmol), and potassium carbonate (129 mg, 0.93 mmol) were suspended in DMF (1 mL), and stirred for 20 minutes at 150° C. in the microwave. The reaction mixture was diluted with MeOH, filtered, and purified via prep-LC-MS to provide 90 (2 mg, 3% yield) as a solid. LC-MS (M+H=381, obsd.=381). 1H NMR (400 MHz, d6-DMSO): δ 11.88 (s, 1H), 8.88 (dd, 1H), 8.50 (dd, 1H), 8.26 (d, 1H), 8.10 (d, 1H), 7.77 (m, 1H), 7.56 (m, 2H), 7.38 (m, 3H), 5.38 (s, 2H).

Workup

  1. filtrationfiltered
  2. custompurified via prep-LC-MS

Sources & evidence

ORD record
ord-c971b6b3291e4edbb02a527892343680
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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