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

HRID 1686075Notes

Reaction equation

HRID 1686075 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 152416121,1`-Bis(diphenylphosphino)ferroceneCatalystHCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-07beba5490b74f22a52d10b88e7519de
Source dataset
uspto-grants-2012_04
Patent number
US08148535B2

Reaction notes

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