Sodium Carbonate → 4-(6-Phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

HRID 1851148Notes

Reaction equation

HRID 1851148 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]2[CH:14]=[CH:15][N:16]=[C:4]2[N:3]=1.[CH:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.ClCCl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:8]1([C:7]2[C:2]([C:22]3[CH:23]=[CH:24][C:19]([CH:17]=[O:18])=[CH:20][CH:21]=3)=[N:3][C:4]3[N:5]([CH:14]=[CH:15][N:16]=3)[CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 772315047-Chloro-6-phenylimidazo[1,2-a]pyrimidine

Product 1

HCID 866306554-(6-Phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 6 g of the crude product obtained in step 3 and 5.1 g 4-formylphenylboronic acid in 210 mL 1,2-dimethoxyethane were added 0.96 g dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct and 42 mL of a 10% w/w sodium carbonate solution. The resulting mixture was heated to 80° C. under an inert gas atmosphere for 15 h. The work up was performed by diluting the reaction mixture with water and dichloromethane, separating the phases and extraction of the aqueous phase with dichloromethane. The combined organic layers were dried over sodium sulphate and evaporated. The residue was suspended in ethyl acetate and the resulting mixture stirred for 2 h at room temperature. The product was collected by filtration and used without further purification.

Workup

  1. customseparating
  2. extractionthe phases and extraction of the aqueous phase with dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. customevaporated
  5. filtrationThe product was collected by filtration
  6. customused without further purification

Sources & evidence

ORD record
ord-2b2af16f0397456bab5ee02b7d88e13d
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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