Sodium Carbonate → 4-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

HRID 1851191Notes

Reaction equation

HRID 1851191 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[N:14]=[CH:15][CH: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]([N:14]=[CH:15][CH: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 866306645-Chloro-6-phenylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 866306654-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-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 300 mg of the mixture from step 3 and 360 mg 4-formylphenylboronic acid in 9 mL 1,2-dimethoxyethane were added 1.8 mL of a 10% w/w sodium carbonate solution and 36 mg dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) and the resulting mixture was heated to 80° C. under an inert gas atmosphere for 18 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, evaporated and the residue was purified by chromatography on silica gel (dichloromethane/methanol). The product was crystallized from ethyl acetate.

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. customthe residue was purified by chromatography on silica gel (dichloromethane/methanol)
  6. customThe product was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-9e342c6e86044594902db3f21420271c
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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