Iodobenzene → N2-methyl-N3-phenylpyridine-2,3-diamine

HRID 333562노트

반응식

HRID 333562 반응식
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][N:4]=1.I[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC([O-])(C)C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC=C3C=2C(C2C4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C=CC=2)=CC=C3)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3]1[C:8]([NH:9][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=[CH:5][N:4]=1

참가 물질

7

반응물 4

HCID 11575IodobenzeneHCID 99390178,8'-Bis(diphenylphosphino)-1,1'-binaphthaleneHCID 123436692-N-methylpyridine-2,3-diamineHCID 23676156Sodium t-butoxide

생성물 1

HCID 68205838N2-methyl-N3-phenylpyridine-2,3-diamine

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

N2-methylpyridine-2,3-diamine (11.95 g, 97 mmol), iodobenzene (16.22 ml, 146 mmol), sodium 2-methylpropan-2-olate (13.99 g, 146 mmol), 8,8′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP) (60.4 g, 97 mmol) with toluene (400 mL) were added to a three necked 1 L round bottom flask. The reaction was degassed with N2 for 20 minutes. Pd2(dba)3 (1.777 g, 1.941 mmol) was added and the reaction mixture was refluxed for 20 h. The reaction mixture was concentrated to dryness. Residue was dissolved in EtOAc. It was not clear solution, but a suspension was obtained and then filtered through a silica gel plug. The desired product was concentrated and recrystallized from DCM/hexanes providing a yield of 6.45 g, 33.3%.

후처리

  1. customThe reaction was degassed with N2 for 20 minutes
  2. temperaturethe reaction mixture was refluxed for 20 h
  3. concentrationThe reaction mixture was concentrated to dryness
  4. dissolutionResidue was dissolved in EtOAc
  5. customa suspension was obtained
  6. filtrationfiltered through a silica gel plug
  7. concentrationThe desired product was concentrated
  8. customrecrystallized from DCM/hexanes providing a yield of 6.45 g, 33.3%

출처 및 근거

ORD 기록
ord-ece73c7210ac4131bad4f9c6528c419a
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883322B2

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