Ethyl Acetate → HCID 58853204, compound

HRID 659980Notes

Reaction equation

HRID 659980 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15](C)[CH:14]=2)[CH2:10][CH2:11][CH3:12])[CH:5]=[N:4][CH:3]=1.[CH3:20]C1(C)C(C)(C)OB(C2C=CC(O)=CC=2)O1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(O)CC.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:13]2[CH:14]=[CH:15][C:16]([CH3:20])=[CH:17][CH:18]=2)[CH2:10][CH2:11][CH3:12])[CH:5]=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 58853220HCID 58853220, compound

Product 1

HCID 58853204HCID 58853204, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 22495535HCID 22495535, compoundSolvent

Procedure

Under a nitrogen atmosphere a mixture of 6-chloro-N-[1-(3-methylphenyl)butyl]pyrazin-2-amine (0.21 g, 0.76 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (0.23 g, 91 mmol), tetrakis(triphenylphosphine)palladium(0) (90 mg, 0.08 mmol) in toluene-n-propanol (4 mL, 3:1) was treated with 2M aqueous sodium carbonate solution (0.4 mL, 0.84 mmol). The resulting mixture was stirred vigorously whilst being heated under reflux for 22 hours. Once cool ethyl acetate was added and the mixture dried (MgSO4) and filtered. Removal of solvent in vacuo then yielded crude product, which was purified by column chromatography using dichloromethane:diethyl ether (90:10) as eluent to furnish (0.165 g, 60%).

Workup

  1. temperaturewhilst being heated
  2. temperatureunder reflux for 22 hours
  3. dry with materialthe mixture dried (MgSO4)
  4. filtrationfiltered
  5. customRemoval of solvent in vacuo
  6. customthen yielded crude product, which
  7. customwas purified by column chromatography
  8. customto furnish (0.165 g, 60%)

Sources & evidence

ORD record
ord-6f8a1a40789245b195a889039a5c3397
Source dataset
uspto-grants-2011_12
Patent number
US08084456B2

Reaction notes

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