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

HRID 1915541Notes

Reaction equation

HRID 1915541 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 (prepared as described under example 11), 180 mg K2CO3, 215 mg Et4NCl, 25 mg PdCl2(PPh3)2 and 620 mg tributyl(vinyl)stannane are suspended in 10 ml THF. The mixture is heated to 110° C. for 45 min. This mixture is worked up by diluting with water and extraction with dichloromethane. The organic layers are dried over Na2SO4 and concentrated to yield the crude product, which is purified by chromatography on silica gel (ethyl acetate/dichloromethane).

Workup

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

Sources & evidence

ORD record
ord-4f3e06e45a4d4f3fb2ae3ba43269f757
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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