Potassium Carbonate → HCID 58168104, compound

HRID 1029074Notes

Reaction equation

HRID 1029074 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7](=[O:15])[C:6]=2[CH:16]=1.FC1C=CC(B(O)O)=CC=1.C1(P(C2CCCCC2)C2C=CC=CC=2[C:40]2[C:45]([O:46][CH3:47])=[CH:44][CH:43]=[CH:42][C:41]=2OC)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:47][O:46][C:45]1[CH:40]=[CH:41][C:42]([C:2]2[CH:3]=[CH:4][C:5]3[C:14]4[C:9](=[N:10][CH:11]=[CH:12][CH:13]=4)[NH:8][C:7](=[O:15])[C:6]=3[CH:16]=2)=[CH:43][CH:44]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 58168076HCID 58168076, compound

Product 1

HCID 58168104HCID 58168104, compoundYield 165.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

8-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 4-fluorophenylboronic acid (61 mg, 0.43 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (7 mg, 0.02 mmol), and potassium carbonate (90 mg, 0.65 mmol) were dissolved in dioxane/H2O (2.2 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, filtered through a membrane plug, and purified via prep-LC-MS to provide 15 (10 mg, 16% yield) as a white solid. LC-MS (M+H=291, obsd.=291). 1H NMR (400 MHz, d6-DMSO): δ 12.15 (s, 1H), 8.88 (dd, 1H), 8.64 (d, 1H), 8.54 (dd, 1H), 8.52 (dd, 1H), 8.22 (dd, 1H), 7.90 (m, 2H), 7.37 (m, 3H).

Workup

  1. filtrationfiltered through a membrane plug
  2. custompurified via prep-LC-MS

Sources & evidence

ORD record
ord-88a7030d588f449e91f3c839f0036c62
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

Loading…