Ethanol → 3-(4-Pyrazinylphenyl)-2-propvn-1-ol

HRID 2416539Notes

Reaction equation

HRID 2416539 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)C.[OH:17][CH2:18][C:19]#[C:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[N:3]1[CH:4]=[CH:5][N:6]=[CH:7][C:2]=1[C:24]1[CH:25]=[CH:26][C:21]([C:20]#[C:19][CH2:18][OH:17])=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 73277ChloropyrazineHCID 22630943[4-(3-hydroxy-1-propynyl)phenyl]boronic Acid

Product 1

HCID 226308173-(4-Pyrazinylphenyl)-2-propvn-1-olYield 66.5%

Reagents, catalysts & solvents 3

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Chloropyrazine (0.78 mL, 8.73 mmol), 1 M aq. Na2CO3 (10 mL), and ethanol (5 mL) were successively added to a mixture of [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.30 g, 0.50 mmol) and [4-(3-hydroxy-1-propynyl)phenyl]boronic acid (1.85 g, 10.51 mmol, prepared as described in Reference Example 235) in toluene (20 mL) and the resulting mixture was heated to reflux for 3 h. The cooled reaction mixture was diluted with ethyl acetate (50 mL) and the organic layer was separated, washed with brine (50 mL), dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 97:3 dichloromethane/methanol) followed by a second chromatography (SiO2, 1:1 hexane/ethyl acetate) provided 1.22 g (66%) of the title compound as a colorless solid. MS 211 (M+H)+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 3 h
  3. customThe cooled reaction mixture
  4. customthe organic layer was separated
  5. washwashed with brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customPurification by chromatography (SiO2, 97:3 dichloromethane/methanol)

Sources & evidence

ORD record
ord-910bfd1073d344d8b0dbe1c0e860457a
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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