Toluene → HCID 58934273, compound

HRID 1817283Notes

Reaction equation

HRID 1817283 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[CH:16]=[N:15][CH:14]=[C:13]([Cl:17])[N:12]=2)[CH3:9])=[CH:4][CH:3]=1.B1([C:24]2[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=2)OCCCO1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CO.ClCCl.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:17][C:13]1[N:12]=[C:11]([NH:10][C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[CH:3][CH:4]=2)[CH3:9])[CH:16]=[N:15][CH:14]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 58934266HCID 58934266, compound

Product 1

HCID 58934273HCID 58934273, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere a mixture of N-[(1S)-1-(4-bromophenyl)ethyl]-6-chloropyrazin-2-amine (0.117 g, 0.37 mmol), pyridine-3-boronic acid 1,3-propanediol cyclic ester (67 mg, 0.41 mmol), tetrakis(triphenylphosphine)palladium(0) (65 mg, 0.06 mmol) and toluene (4 mL) was treated with 2M aqueous sodium carbonate solution (0.2 mL). The resulting mixture was stirred vigorously whilst being heated under reflux for 24 hours. Upon cooling, the solution was diluted with methanol and dichloromethane and the mixture dried (MgSO4) and filtered. Removal of solvent in vacuo then yielded the crude product which was purified by column chromatography using dichloromethane-diethyl ether (90:10) then dichloromethane-methanol (99:1) as eluent (50 mg).

Workup

  1. temperaturewhilst being heated
  2. temperatureunder reflux for 24 hours
  3. temperatureUpon cooling
  4. dry with materialthe mixture dried (MgSO4)
  5. filtrationfiltered
  6. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-c86b582c4f3f47ebbf023bedccb7eca3
Source dataset
uspto-grants-2009_10
Patent number
US07598272B2

Reaction notes

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