Water → 2-(2-bromo-5-(trifluoromethyl)phenyl)-1-methyl-1H-imidazole

HRID 1473361노트

반응식

HRID 1473361 반응식
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[Sn](CCCC)(CCCC)CCCC.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=1I.[F-].[K+].O>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].C(Cl)Cl>[Br:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][C:26]=1[C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 522689Potassium FluorideHCID 27632521-Methyl-2-(tributylstannyl)-1H-imidazoleHCID 467352311-Bromo-2-iodo-4-(trifluoromethyl)benzene

생성물 1

HCID 866874082-(2-bromo-5-(trifluoromethyl)phenyl)-1-methyl-1H-imidazole수율 64.6%

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of PdCl2(dppf)-CH2Cl2 adduct (0.233 g, 0.285 mmol), 1-methyl-2-(tributylstannyl)imidazole (2.189 ml, 6.84 mmol), 1-bromo-2-iodo-4-(trifluoromethyl)benzene (0.919 ml, 5.70 mmol), and potassium fluoride (1.656 g, 28.5 mmol) in 6 mL DMF was heated to 80° C. overnight. LC/MS showed product, so the reaction mixture was poured into water and was extracted with DCM. The organics were dried over MgSO4 and concentrated. Purification of the crude residue by silica gel column chromatography (0 to 100% EtOAc/heptane) gave 2-(2-bromo-5-(trifluoromethyl)phenyl)-1-methyl-1H-imidazole (1.122 g, 3.68 mmol, 64.5% yield). m/z (ESI) 307.2 (M+H)+.

후처리

  1. extractionwas extracted with DCM
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customPurification of the crude residue by silica gel column chromatography (0 to 100% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-4c79b97521bf4dbaa0dbc838e75f0a0e
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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