Sodium Carbonate → 2,5-Dimethyl-4-(pyridin-3-yl)aniline

HRID 536348노트

반응식

HRID 536348 반응식
Br[C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13](B(O)O)[CH:12]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C([O-])([O-])=O.[Na+].[Na+]>CCCCO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:10][C:4]1[CH:3]=[C:2]([C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)[C:8]([CH3:9])=[CH:7][C:5]=1[NH2:6]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 81671304-Bromo-2,5-dimethylanilineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

생성물 1

HCID 582571172,5-Dimethyl-4-(pyridin-3-yl)aniline

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 2631-Butanol용매

실험 절차

A suspension of 4-bromo-2,5-dimethylaniline (4.00 g, 20 mmol), pyridin-3-ylboronic acid (2.70 g, 11 mmol), Pd2(dba)3 (0.55 g, 0.6 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.98 g, 1.2 mmol) and Na2CO3 (10.6 g, 100 mmol) in n-BuOH (50 mL) was degassed by a stream of argon gas for 15 min. The reaction flask was sealed and placed in a pre-heated oil bath (115° C.). After stirring overnight, the reaction was cooled and filtered. The filter cake was washed with DCM and the filtrate was concentrated in vacuo. The resulting residue was dissolved in EtOAc (150 mL). EtOAC was sequentially washed with water (20 mL), brine (20 mL), dried over Na2SO4 and evaporated. The crude product was purified by silica chromatography (0-50% EtOAC in hexanes gradient) to give 2,5-dimethyl-4-(pyridin-3-yl)aniline as a yellow solid; ESMS m/z 199.1 (M+H+).

후처리

  1. customwas degassed by a stream of argon gas for 15 min
  2. customThe reaction flask was sealed
  3. customplaced in a pre-heated oil bath
  4. custom(115° C.)
  5. temperaturethe reaction was cooled
  6. filtrationfiltered
  7. washThe filter cake was washed with DCM
  8. concentrationthe filtrate was concentrated in vacuo
  9. dissolutionThe resulting residue was dissolved in EtOAc (150 mL)
  10. washEtOAC was sequentially washed with water (20 mL), brine (20 mL)
  11. dry with materialdried over Na2SO4
  12. customevaporated
  13. customThe crude product was purified by silica chromatography (0-50% EtOAC in hexanes gradient)

출처 및 근거

ORD 기록
ord-e90390f522e44009a109bc17cbc662f6
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859574B2

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