Dibutyltin dichloride → Methyl 4-{[methyl(pyridin-2-yl)amino]methyl}benzoate

HRID 606578Notes

Reaction equation

HRID 606578 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[CH3:9][O:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1>[CH3:1][N:2]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([O:10][CH3:9])=[O:20])=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 15294Methyl 4-FormylbenzoateHCID 207272-Pyridinamine, N-methyl-

Product 1

HCID 67046855Methyl 4-{[methyl(pyridin-2-yl)amino]methyl}benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methylaminopyridine (1.0 mmol) and methyl-4-formylbenzoate (1.0 mmol) were mixed in THF (2 mL) and dibutyltin dichloride (0.1 mmol) was added. After stirring at RT for 10 minutes, phenylsilane (1.1 mmol) was added and the reaction mixture allowed to stir at room temperature for a further 17 h. The reaction mixture was then concentrated by N2 stream and the residue purified by flash chromatography (silica gel, heptane:EtOAc) to give methyl 4-[methyl(pyridin-2-yl)amino]methylbenzoate: m/z=257 in MS ES+ as a yellow oil which was used directly in the subsequent step.

Workup

  1. stirringto stir at room temperature for a further 17 h
  2. concentrationThe reaction mixture was then concentrated by N2 stream
  3. customthe residue purified by flash chromatography (silica gel, heptane:EtOAc)

Sources & evidence

ORD record
ord-128f496b73e448d39effbc1e2baf9dd9
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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