Potassium Carbonate → HCID 86630295, compound

HRID 884072Notes

Reaction equation

HRID 884072 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[C:2]#[C:3][CH2:4][CH3:5].I[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][O:19][CH3:20])[CH:12]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.O>[CH3:20][O:19][CH2:18][O:17][C:13]1[CH:12]=[C:11](/[C:2](=[C:3](\[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)/[CH2:4][CH3:5])/[C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 99169Ethyl pent-2-yn-1-oateHCID 21101203HCID 21101203, compound

Product 1

HCID 86630295HCID 86630295, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Ethyl 2-pentynoate (350 mg, 2.77 mmol), 1-iodo-3-(methoxymethoxy)benzene (1.46 g, 5.53 mmol), Phenylboronic acid (675 mg, 5.54 mmol) and K2CO3 (766 mg, 5.54 mmol) in DMF (8 ml)-H2O (2 ml) was stirred at room temperature for 10 min. Then PdCl2(PhCN)2 (10.6 mg, 0.0276 mmol) was added under Ar atmosphere, and the mixture was stirred at room temperature for 24 h. The reaction was quenched with H2O under ice cooling, and the whole was extracted with Et2O. The organic layer was washed with H2O, brine, dried over Na2SO4, then concentrated. Purification by Biotage HPFC (eluent: hexane to hexane/AcOEt, 10:1) gave 2a (25%). 2a: colorless oil; 1H-NMR (CDCl3) δ 1.02 (3H, t, J=7.4 Hz), 1.31 (3H, t, J=7.2 Hz), 2.65 (2H, t, J=7.4 Hz), 3.33 (3H, s), 4.29 (2H, t, J=7.2 Hz), 4.91 (2H, s), 6.65 (1H, m), 6.68 (1H, m), 6.74 (1H, ddd, J=1.0, 2.5, 8.3 Hz), 7.00-7.05 (3H, m), 7.10-7.19 (3H, m).

Workup

  1. stirringthe mixture was stirred at room temperature for 24 h
  2. customThe reaction was quenched with H2O under ice cooling
  3. extractionthe whole was extracted with Et2O
  4. washThe organic layer was washed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by Biotage HPFC (eluent: hexane to hexane/AcOEt, 10:1)

Sources & evidence

ORD record
ord-8d7362547399469e80e3420885cea25b
Source dataset
uspto-grants-2012_08
Patent number
US08236987B2

Reaction notes

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