Potassium Carbonate → HCID 178516131, compound

HRID 269383Notes

Reaction equation

HRID 269383 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:6]=[C:5]2[OH:16].C([O-])([O-])=O.[K+].[K+].[O:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH:25]=[C:24]1B(O)O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[O:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH:25]=[C:24]1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:6]=[C:5]2[OH:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 178516130HCID 178516130, compound

Product 1

HCID 178516131HCID 178516131, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a flask with 6-bromo-4-hydroxy-2-trifluoromethyl-quinoline (1.00 g, 3.42 mmol) was added K2CO3 (8.55 mL, 1.0 M in H2O, 8.55 mmol) followed by dioxane (85.5 mL). Benzofuran-2-boronic acid (0.665 g, 4.10 mmol) was then added followed by PdCl2(dppf) (0.028 g, 0.0342 mmol). The reaction mixture was stirred at room temperature for 0.5 hour and then heated to 65° C. for 18 hours. After concentration, the reaction was diluted with EtOAc (200 mL). The organic layer was washed with 1 N HCl, (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL) and then dried (MgSO4). After concentration, the residue was recrystallized from EtOAc to afford the product (0.770 g, 68%) as a solid. Mass spectrum (+ESI, [M+H]+) m/z 330. 1H NMR (500 MHz, DMSO-d6): δ 8.68 (s, 1H), 8.37 (d, 1H, J=9.3 Hz), 8.07 (d, 1H, J=9.3 Hz), 7.65-7.75 (m, 3H), 7.38 (t, 1H, J=7.7 Hz), 7.30 (t, 1H, J=7.7 Hz), and 7.06 ppm (s, 1H).

Workup

  1. temperatureheated to 65° C. for 18 hours
  2. concentrationAfter concentration
  3. additionthe reaction was diluted with EtOAc (200 mL)
  4. washThe organic layer was washed with 1 N HCl, (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationAfter concentration
  7. customthe residue was recrystallized from EtOAc

Sources & evidence

ORD record
ord-071f9176593848699508ae81620e466b
Source dataset
uspto-grants-2008_11
Patent number
US07446201B2

Reaction notes

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