Sodium Carbonate → HCID 86630694, compound

HRID 503794Notes

Reaction equation

HRID 503794 reaction equation
[Br:1][C:2]1[N:17]=[C:5]2[N:6]=[C:7](Cl)[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:9][N: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]>[Br:1][C:2]1[N:17]=[C:5]2[N:6]=[C:7]([C:23]3[CH:24]=[CH:25][C:20]([CH:18]=[O:19])=[CH:21][CH:22]=3)[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 86630692HCID 86630692, compound

Product 1

HCID 86630694HCID 86630694, 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 1.0 g 2-bromo-5-chloro-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine and 0.48 g 4-formylphenylboronic acid in 10 ml 1,2-dimethoxyethane are added 6.2 ml of a 10% w/w sodium carbonate solution and 118 mg dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) and the resulting mixture is heated to 100° C. by microwave irradiation under a inert gas atmosphere for 50 min. The work up is 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 are dried over Na2SO4 and the solvent is evaporated. The crude product is purified by chromatography on silica gel (dichloromethane/ethyl acetate) 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 are dried over Na2SO4
  4. customthe solvent is evaporated
  5. customThe crude product is purified by chromatography on silica gel (dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-307d49ac55c94236bb9c73b491de2ac4
Source dataset
uspto-grants-2010_08
Patent number
US07776864B2

Reaction notes

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