Potassium Carbonate → HCID 117630821, compound

HRID 1750564Notes

Reaction equation

HRID 1750564 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O)#[N:16]>CN(C=O)C.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:8][C:5]1[CH:4]=[N:3][C:2]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:15]#[N:16])=[N:7][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27346102-Cyanophenylboronic acidHCID 263440482-Bromo-5-fluoropyrimidine

Product 1

HCID 117630821HCID 117630821, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-bromo-5-fluoropyrimidine (CAS number 947533-45-1; 301 mg, 1.70 mmol), potassium carbonate (705 mg, 5.10 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (62 mg, 0.085 mmol) in DMF (5 ml) was purged and evacuated with nitrogen. To this was then added (2-cyanophenyl)boronic acid (CAS number 138642-62-3; 300 mg, 2.04 mmol) and the reaction was subjected to microwave irradiation at 140° C. for 10 minutes and then at 130° C. for 35 minutes. The reaction was partitioned between ethyl acetate (50 ml) and water (50 ml) and filtered through diatomaceous earth (commercially sold under the trade mark “Celite”). The organics were washed with brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified column chromatography (silica, 0-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customwas purged
  2. customevacuated with nitrogen
  3. customirradiation at 140° C. for 10 minutes
  4. customThe reaction was partitioned between ethyl acetate (50 ml) and water (50 ml)
  5. filtrationfiltered through diatomaceous earth (
  6. washThe organics were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified column chromatography (silica, 0-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-8c69f9ec628443b1adb97ec0c5301292
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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