Sodium Carbonate → HCID 86630694, compound

HRID 1851219Notes

Reaction equation

HRID 1851219 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 were 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 was heated to 100° C. by microwave irradiation under a inert gas atmosphere for 50 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 Na2SO4 and the solvent was evaporated. The crude product was 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 were dried over Na2SO4
  4. customthe solvent was evaporated
  5. customThe crude product was purified by chromatography on silica gel (dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-38ec3f8118f04d8183813fc0adb65b74
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

Loading…