Sodium Carbonate → 2-[2-(4-Fluorophenyl)-1,3-oxazol-4-yl]pyrimidine

HRID 1469388

Reaction equation

HRID 1469388 reaction equation
FC(F)(F)S(O[C:7]1[N:8]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[O:10][CH:11]=1)(=O)=O.C([O-])(=O)C.[Na+].B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.Br[C:45]1[N:50]=[CH:49][CH:48]=[CH:47][N:46]=1.C(=O)([O-])[O-].[Na+].[Na+]>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].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[O:10][CH:11]=[C:7]([C:45]3[N:50]=[CH:49][CH:48]=[CH:47][N:46]=3)[N:8]=2)=[CH:13][CH:14]=1

Participants

10

Reactant 5

HCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 517045Sodium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 116595992-(4-Fluorophenyl)oxazol-4-yl trifluoromethanesulfonate

Product 1

HCID 894857232-[2-(4-Fluorophenyl)-1,3-oxazol-4-yl]pyrimidine

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of 2-(4-fluorophenyl)-1,3-oxazol-4-yl trifluoromethanesulfonate (3.8 g, 12.21 mmol), Fe(dppf)2 (0.338 g, 0.611 mmol), Pd(dppf)Cl2 (0.447 g, 0.611 mmol), sodium acetate and bis(pinacolato)diboron (4.03 g, 15.87 mmol) in 50 ml of dioxane was heated at 100° C. for 3 h. Then 2-bromopyrimidine (2.91 g, 18.32 mmol), Pd(PPh3)2Cl2 (0.857 g, 1.221 mmol) and sodium carbonate (12.2 ml, 2 M, 2.42 mmol) were added. The resultant mixture was then heated at 95° C. overnight, diluted with H2O and extracted with EtOAc. The organic extract was washed with brine, dried over MgSO4, filtered, and the filtrate was concentrated. The resulting residue was purified by flash chromatography (silica gel column, EtOAc/hexane) to give the title compound. LC-MS m/z 241.11 [M+1]+.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe resulting residue was purified by flash chromatography (silica gel column, EtOAc/hexane)

Sources & evidence

ORD record
ord-b15224f715f344bcb1747f3dd9317aa9
Source dataset
uspto-grants-2015_04
Patent number
US09006268B2

Linked notes

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