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

HRID 1473361ノート

反応式

HRID 1473361 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-4c79b97521bf4dbaa0dbc838e75f0a0e
出典データセット
uspto-grants-2015_04
特許番号
US09012443B2

反応ノート

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