Water → 2-{6-[5-(Pyridin-3-yl)-3-furyl]pyridin-2-yl}pyrimidine

HRID 705034Notes

Reaction equation

HRID 705034 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[O:12][CH:13]=2)O1.Br[C:22]1[N:27]=[C:26]([C:28]2[N:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:11]2[O:12][CH:13]=[C:9]([C:22]3[N:27]=[C:26]([C:28]4[N:29]=[CH:30][CH:31]=[CH:32][N:33]=4)[CH:25]=[CH:24][CH:23]=3)[CH:10]=2)[CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 158812582-(6-Bromopyridin-2-yl)pyrimidineHCID 690926343-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-furyl]pyridine

Product 1

HCID 675133672-{6-[5-(Pyridin-3-yl)-3-furyl]pyridin-2-yl}pyrimidineYield 50%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

400 mg (1.38 mmol) of 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-furyl]pyridine and 347 mg (1.38 mmol) of 2-(6-bromopyridin-2-yl)pyrimidine were initially charged in 20 ml of dioxane, and 3.46 ml of a 2 molar aqueous sodium carbonate solution were added. The reaction mixture was degassed in an ultrasonic bath under argon and then heated to reflux temperature, and, at 80° C., 48.0 mg (42.0 μmol) of tetrakis(triphenylphosphine)palladium(0) were added. The reaction mixture was stirred under reflux for 8 hours and then at room temperature overnight. The mixture was then poured into 100 ml of water and extracted with dichloromethane. The light-yellow organic phases were combined, washed with 100 ml of water and then dried over MgSO4. The mixture was then filtered and concentrated under reduced pressure on a rotary evaporator. Chromatographic purification gave 206 mg (50% of theory) of 2-{6-[5-(pyridin-3-yl)-3-furyl]pyridin-2-yl}pyrimidine.

Workup

  1. customThe reaction mixture was degassed in an ultrasonic bath under argon
  2. temperatureheated
  3. temperatureto reflux temperature
  4. temperatureunder reflux for 8 hours
  5. customat room temperature
  6. customovernight
  7. extractionextracted with dichloromethane
  8. washwashed with 100 ml of water
  9. dry with materialdried over MgSO4
  10. filtrationThe mixture was then filtered
  11. concentrationconcentrated under reduced pressure on a rotary evaporator
  12. customChromatographic purification

Sources & evidence

ORD record
ord-6f6106b0e78c4122a50bfaefaf7e236d
Source dataset
uspto-grants-2015_11
Patent number
US09173396B2

Reaction notes

Loading…