2-Fluoroaniline → HCID 69813141, compound

HRID 1029075Notes

Reaction equation

HRID 1029075 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.F[C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC(C)([O-])C.[Na+]>O1CCOCC1.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:19]1([NH:20][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:21]=[CH:22][CH:23]=[CH:24][CH:18]=1

Participants

8

Reactant 4

HCID 95842-FluoroanilineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 58168076HCID 58168076, compound

Product 1

HCID 69813141HCID 69813141, compoundYield 39.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

8-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 2-fluoroaniline (48 mg, 0.43 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (8 mg, 0.02 mmol), and sodium tert-butoxide (63 mg, 0.65 mmol) were suspended in dioxane (2 mL), 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 17 (25 mg, 38% yield) as a tan solid. LC-MS (M+H=306, obsd.=306). 1H NMR (400 MHz, d6-DMSO): δ 11.92 (s, 1H), 8.66 (dd, 1H), 8.58 (s, 1H), 8.39 (m, 2H), 7.75 (d, 1H), 7.44 (m, 2H), 7.32 (dd, 1H), 7.28 (dd, 1H), 7.21 (dt, 1H), 7.11 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-c5051a783206479696244f8d73bbbb89
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

Loading…