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

HRID 1767609노트

반응식

HRID 1767609 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-a6420ce983a8419ca6a9dc7af2f929c8
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07235548B2

반응 노트

불러오는 중…