Potassium Carbonate → 4-(6-Phenyl-3-vinylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

HRID 1851179Notes

Reaction equation

HRID 1851179 reaction equation
Br[C:2]1[N:6]2[CH:7]=[C:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:9]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=3)=[N:10][C:5]2=[N:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:31]([Sn](CCCC)(CCCC)C=C)[CH2:32]CC>[N+](CC)(CC)(CC)CC.[Cl-].C1COCC1.O.ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:19]1([C:8]2[C:9]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=3)=[N:10][C:5]3[N:6]([C:2]([CH:31]=[CH2:32])=[CH:3][N:4]=3)[CH:7]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 3

HCID 11430Potassium CarbonateHCID 81998TributylvinyltinHCID 866306584-(3-Bromo-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Product 1

HCID 866306634-(6-Phenyl-3-vinylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Reagents, catalysts & solvents 5

HCID 5946Tetraethylammonium ChlorideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

500 mg 4-(3-bromo-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde, 180 mg K2CO3, 215 mg Et4NCl, 25 mg PdCl2(PPh3)2 and 620 mg tributyl(vinyl)stannane were suspended in 10 mL THF. The mixture was heated to 110° C. for 45 min. This mixture was worked up by diluting with water and extraction with dichloromethane. The organic layers were dried over Na2SO4 and concentrated to yield the crude product, which was purified by chromatography on silica gel (ethyl acetate/dichloromethane).

Workup

  1. dry with materialThe organic layers were dried over Na2SO4
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-1417b05f91f949dba3f916dc9bc8bfbd
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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