Stannane, trimethylphenyl- → Tert-butyl (2-oxo-1-phenyl-1,2-dihydropyridin-4-ylmethyl)-carbamate

HRID 2236880Notes

Reaction equation

HRID 2236880 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=[CH:4][NH:3]1.C[Sn](C)(C)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH:5]=[CH:4][N:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 123095Stannane, trimethylphenyl-HCID 2724141Tetrabutylammonium FluorideHCID 426256764-(Boc-aminomethyl)-1H-pyridin-2-one

Product 1

HCID 42625677Tert-butyl (2-oxo-1-phenyl-1,2-dihydropyridin-4-ylmethyl)-carbamateYield 52%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2-oxo-1,2-dihydro-pyridin-4-ylmethyl)-carbamate (0.13 g, 0.58 mmol) in dichloromethane (5 mL) is added trimethylphenylstannane (210 μL, 1.2 mmol), followed successively by copper (II) acetate (0.12 g, 0.64 mmol) and tetra-n-butylammonium fluoride (1.0 M solution in tetrahydrofuran, 1.2 mL). The reaction mixture is stirred for 2 days at room temperature and then is quenched by the addition of methanolic ammonia (2 M, 4 mL). The reaction mixture is concentrated and then purified by flash silica gel chromatography (methanol/chloroform) to give tert-butyl (2-oxo-1-phenyl-1,2-dihydropyridin-4-ylmethyl)-carbamate (88 mg, 52%).

Workup

  1. customis quenched by the addition of methanolic ammonia (2 M, 4 mL)
  2. concentrationThe reaction mixture is concentrated
  3. custompurified by flash silica gel chromatography (methanol/chloroform)

Sources & evidence

ORD record
ord-056be2815ca043cc858c2ebb0cca2b5e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…