Sodium Carbonate → HCID 86630689, compound

HRID 1851213Notes

Reaction equation

HRID 1851213 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]=[C:15]([CH3:17])[CH:16]=[C:4]2[N:3]=1.[CH:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:19].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]>[CH3:17][C:15]1[CH:16]=[C:4]2[N:3]=[C:2]([C:23]3[CH:24]=[CH:25][C:20]([CH:18]=[O:19])=[CH:21][CH:22]=3)[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][N:5]2[N:14]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 86630688HCID 86630688, compound

Product 1

HCID 86630689HCID 86630689, compound

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
100 °C

Procedure

To a mixture of 1.35 g of 5-chloro-2-methyl-6-phenylpyrazolo[1,5-a]pyrimidine and 1.04 g 4-formylphenylboronic acid in 20 mL 1,2-dimethoxyethane were added 10.8 mL of a 10% w/w sodium carbonate solution and 120 mg dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II). The resulting mixture was heated to 100° C. by microwave irradiation under an inert gas atmosphere for 75 min. 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 crude product was purified by chromatography on silica gel (dichloromethane/methanol) to yield the desired product.

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 crude product was purified by chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record
ord-651e7e823fbd4f2095d32c3e50041c7e
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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