Potassium Fluoride → HCID 68958235, compound

HRID 269389Notes

Reaction equation

HRID 269389 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:16]=[C:15]1B(O)O.[F-].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1COCC1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:16]=[C:15]1[C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

8

Reactant 4

HCID 522689Potassium FluorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 2776266Benzo[b]furan-2-boronic acidHCID 134045925-Chloro-8-methoxyquinoline

Product 1

HCID 68958235HCID 68958235, compoundYield 62.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-chloro-8-methoxy-quinoline (0.330 g, 1.70 mmol) in THF (2 mL) at room temperature was added benzofuran-2-boronic acid (0.413 g, 2.55 mmol) followed by KF (0.296 mL, 5.10 mmol), Pd(OAc)2 (0.0382 g, 0.170 mmol), and 2-(di-tert-butyl phosphino)biphenyl (0.101 g, 0.340 mmol). The reaction mixture was stirred at room temperature for 18 hours and then diluted with EtOAc (200 mL). The organic layer was washed with H2O (20 mL) and brine (20 mL) then dried (Na2SO4). After concentration, the residue was purified on a Biotage Flash 40 apparatus (30-70% EtOAc:petroleum ether) to afford the product (0.291 g, 62%) as a solid. Mass spectrum (+ESI, [M+H]+) m/z 276. 1H NMR (500 MHz, DMSO-d6): δ 8.94 (d, 1H, J=2.2 Hz), 8.83 (d, 1H, J=9.4 Hz), 7.99 (d, 1H, J=8.6 Hz), 7.66-7.77 (m, 3H), 7.27-7.41 (m, 4H), and 4.6 ppm (s, 3H).

Workup

  1. washThe organic layer was washed with H2O (20 mL) and brine (20 mL)
  2. dry with materialthen dried (Na2SO4)
  3. concentrationAfter concentration
  4. customthe residue was purified on a Biotage Flash 40 apparatus (30-70% EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-766455aae57e44d0a4de7d78f6ab2011
Source dataset
uspto-grants-2008_11
Patent number
US07446201B2

Reaction notes

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