N-Methyl-3-pyridinamine → 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-N-methyl-N-pyridin-3-ylpyridin-2-amine

HRID 1686075ノート

反応式

HRID 1686075 の反応式
[Si:1]([O:8][CH2:9][C:10]1[C:11](Cl)=[N:12][CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].[CH3:23][NH:24][C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=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].[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2].C1(C)C=CC=CC=1>[Si:1]([O:8][CH2:9][C:10]1[C:11]([N:24]([CH3:23])[C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[N:12][CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

7

反応物 3

HCID 140376N-Methyl-3-pyridinamineHCID 183681113-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridineHCID 23676156Sodium t-butoxide

生成物 1

HCID 672647703-({[tert-butyl(dimethyl)silyl]oxy}methyl)-N-methyl-N-pyridin-3-ylpyridin-2-amine収率 82.9%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 152416121,1`-Bis(diphenylphosphino)ferrocene触媒HCID 1140Toluene溶媒

実験手順

3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridine (1 g), tris(dibenzylideneacetone)-dipalladium(0) (89 mg), 1,1-bis(diphenylphosphino)ferrocene (108 mg), sodium tert-butoxide (559 mg), and 3-(methylamino)pyridine (629 mg) were combined, and 20 mL toluene was added. The mixture was heated 100 C under Ar for 16 h, then cooled to room temperature and filtered through celite, washing with CH2Cl2. The filtrate was concentrated and purified via flash chromatography to give 1.06 g of 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-N-methyl-N-pyridin-3-ylpyridin-2-amine.

後処理

  1. temperatureThe mixture was heated 100 C under Ar for 16 h
  2. filtrationfiltered through celite
  3. washwashing with CH2Cl2
  4. concentrationThe filtrate was concentrated
  5. custompurified via flash chromatography

出典と根拠

ORDレコード
ord-07beba5490b74f22a52d10b88e7519de
出典データセット
uspto-grants-2012_04
特許番号
US08148535B2

反応ノート

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