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

HRID 1469388노트

반응식

HRID 1469388 반응식
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

참가 물질

10

반응물 5

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

생성물 1

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

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-b15224f715f344bcb1747f3dd9317aa9
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006268B2

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