Toluene → HCID 135457320, compound

HRID 1244385Notes

Reaction equation

HRID 1244385 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH:5]=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)O1.C1(C)C=CC=CC=1.[C:40](=O)([O-])[O-:41].[Na+].[Na+]>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.C(OCC)(=O)C>[CH3:40][O:41][C:27]1[CH:26]=[C:25]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([NH:8][C@@H:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH3:10])[N:7]=2)[CH:30]=[CH:29][C:28]=1[OH:31]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 587170826-chloro-N-[(1R)-1-phenylethyl]pyrazin-2-amine

Product 1

HCID 135457320HCID 135457320, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere a mixture of 6-chloro-N-[(1R)-1-phenylethyl]pyrazin-2-amine (0.611 g, 2.61 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (0.785 g, 3.14 mmol), tetrakis(triphenylphosphine)palladium(0) (0.30 g, 0.26 mmol) and toluene (3 mL) was treated with 2M aqueous sodium carbonate solution (1.6 mL, 2.6 mmol). The resulting mixture was stirred vigorously whilst being heated under reflux for 24 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 (99:1→90:10) as eluent: (0.619 g, 74%).

Workup

  1. temperaturewhilst being heated
  2. temperatureunder reflux for 24 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

Sources & evidence

ORD record
ord-006e61b1256241248bb734e69d9c0492
Source dataset
uspto-grants-2006_10
Patent number
US07122550B2

Reaction notes

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