2-Bromopyridine → 3-(2-Pyridyl)aniline

HRID 496099노트

반응식

HRID 496099 반응식
S(O)(O)(=O)=O.[NH2:6][C:7]1[CH:8]=[C:9](B(O)O)[CH:10]=[CH:11][CH:12]=1.[NH2:16][C:17]1C=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.BrC1C=CC=CN=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.C(Cl)Cl.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>[N:16]1[CH:17]=[CH:22][CH:21]=[CH:20][C:19]=1[C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[NH2:6]

참가 물질

7

반응물 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 162111393-Aminophenylboronic Acid Hemisulfate

생성물 1

HCID 4595173-(2-Pyridyl)aniline

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6344Dichloromethane용매HCID 80711,2-Dimethoxyethane용매

실험 절차

3-Aminophenylboronic acid hemisulphate (5.58 g, 30 mmol), 2-bromopyridine (2.7 ml, 28 mmol), Pd(PPh3)2Cl2 (100 mg, 0.5 mol %), 2M K2CO3 (50 ml) were refluxed in 1,2-dimethoxyethane (50 ml) for 24 h under N2. The mixture was diluted with CH2Cl2 (100 ml) and washed with sat. NaHCO3 (50 ml). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure. Flash-chromatography with CH2Cl2 as eluent gave 3-(2-pyridyl)aniline as a yellow oil, 1.0 g (21%). 3-(2-Pyridyl)aniline was transformed by Method B and Method G (using cyclohexanecarboxaldehyde). M.p. 213-216° C.

후처리

  1. washwashed with sat. NaHCO3 (50 ml)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-2687b25969334e55848d52873f0487bc
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943159B1

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