Water → HCID 58337131, compound

HRID 1809176Notes

Reaction equation

HRID 1809176 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([S:11][CH3:12])[C:5]2=[N:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.O(C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[N:6]3[CH:7]=[CH:8][N:9]=[C:10]([S:11][CH3:12])[C:5]3=[N:4][CH:3]=2)=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 578031073-Bromo-8-(methylsulfanyl)imidazo[1,2-a]pyrazine

Product 1

HCID 58337131HCID 58337131, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
88 °C

Procedure

A mixture of 3-Bromo-8-methylsulfanyl-imidazo[1,2-a]pyrazine (1.06 g, 4.33 mmol), 4-methoxybenzeneboronic acid (0.79 g, 5.2 mmol), Pd(OAc)2 (0.05 g, 0.22 mmol), (oxidi-2,1-phenylene)bis(diphenylphosphine) (233 mg, 0.43 mmol), 1.5M K2CO3 in water (5.8 mL, 8.66 mmol) and DMF (12.8 mL) is stirred at 88° C. for 16 h. Then allowed to cool, filtered through cotton, diluted with EtOAc and washed with water and brine. The organic layer is dried with MgSO4 anh., filtered and evaporated. The crude is purified by column chromatography using a gradient of (Pet. Ether 40-60/AcOEt: 7/3 to 1/1) to give 3-(4-Methoxy-phenyl)-8-methylsulfanyl-imidazo[1,2-a]pyrazine as a pale yellow solid (1.0 g, 85%).

Workup

  1. temperatureto cool
  2. filtrationfiltered through cotton
  3. additiondiluted with EtOAc
  4. washwashed with water and brine
  5. dry with materialThe organic layer is dried with MgSO4 anh.
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude is purified by column chromatography

Sources & evidence

ORD record
ord-0187456a0bf84461b855ac6173c31a74
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

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