Potassium Carbonate → HCID 178461418, compound

HRID 1988130Notes

Reaction equation

HRID 1988130 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:11][C@H:10]([N:12]3[CH2:16][CH2:15][CH2:14][C@H:13]3[CH3:17])[CH2:9]2)=[CH:4][CH:3]=1.[C:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)#[N:19].C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:17][C@@H:13]1[CH2:14][CH2:15][CH2:16][N:12]1[C@@H:10]1[CH2:11][C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([C:23]3[CH:24]=[CH:25][C:20]([C:18]#[N:19])=[CH:21][CH:22]=3)=[CH:3][CH:4]=2)[CH2:9]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 178461415HCID 178461415, compound

Product 1

HCID 178461418HCID 178461418, compoundYield 33.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of the product from Example 2A (100 mg, 0.34 mmol), 4-cyanophenyl boronic acid (65 mg, 0.44 mmol), dichlorobis(triphenylphosphine)palladium(II) (12 mg, 17 μmol) and potassium carbonate (120 mg, 0.85 mmol) under an atmosphere of nitrogen in isopropyl alcohol (8 mL) was heated at reflux for 5 hrs. Then, the reaction mixture was cooled to ambient temperature. The mixture was partitioned between ethyl acetate (25 mL) and H2O (10 mL). The organic layer was washed with brine, dried with magnesium sulfate, filtered, concentrated, and chromatographed on silica gel, eluting with 3% (9:1 MeOH:conc NH4OH) in dichloromethane to provide 36 mg of the title compound. 1H NMR (300 MHz, CD3OD) δ 1.21 (d, J=6 Hz, 3 H), 1.54 (m, 1 H), 1.84 (m, 2 H), 2.07 (m, 1 H), 2.18 (m, 2 H), 2.57 (m, 2 H), 2.71 (m, 2 H), 3.11 (m, 1 H), 3.27 (m, 2 H), 7.39 (d, J=9 Hz, 2 H), 7.64 (d, J=9 Hz, 2 H), 7.79 (s, 4 H); (DCl/NH3) m/z 317 (M+H)+.

Workup

  1. temperatureat reflux for 5 hrs
  2. customThe mixture was partitioned between ethyl acetate (25 mL) and H2O (10 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel
  8. washeluting with 3% (9:1 MeOH:conc NH4OH) in dichloromethane

Sources & evidence

ORD record
ord-bebcbf599d8949068272e808fd25c676
Source dataset
uspto-grants-2009_06
Patent number
US07553964B2

Reaction notes

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