Potassium Carbonate → HCID 117727869, compound

HRID 61287Notes

Reaction equation

HRID 61287 reaction equation
[F:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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]>[F:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]([C:23]2[N:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 131737164HCID 131737164, compound

Product 1

HCID 117727869HCID 117727869, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A stirred suspension of methyl 2,3-difluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, 2-chloropyrimidine, PdCl2(dppf) and K2CO3 in 1,4-dioxane and water (3:1, v/v) was heated at 90° C. under nitrogen for 18 h. The reaction mixture was cooled to rt and concentrated under reduced pressure. The resulting residue was directly purified by flash column chromatography on silica gel (0% to 50% EtOAc/hexanes) to give the title compound. ESI MS (M+H) 251.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was directly purified by flash column chromatography on silica gel (0% to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-aaf1f4f67840462a8133d75c9792cfee
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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