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

HRID 1469388ノート

反応式

HRID 1469388 の反応式
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

参加物

10

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-b15224f715f344bcb1747f3dd9317aa9
出典データセット
uspto-grants-2015_04
特許番号
US09006268B2

反応ノート

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