Tributylvinyltin → (2-Methoxy-benzyl)-(5-vinyl-quinolin-2-yl)-amine

HRID 1669716Notes

Reaction equation

HRID 1669716 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])=[N:7]2.[CH:22]([Sn](CCCC)(CCCC)CCCC)=[CH2:23]>C1(C)C=CC=CC=1.C(#N)C>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[CH:22]=[CH2:23])[N:7]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 67334552(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine

Product 1

HCID 44218150(2-Methoxy-benzyl)-(5-vinyl-quinolin-2-yl)-amine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (prepared from 5-bromo-2-chloroquinoline and 2-methoxy-benzylamine as described in example 3, step A, 1 g, 2.9 mmol) was dissolved in 30 mL toluene. Vinyltributyltin (952 mg, 3.0 mmol) and tetrakis(triphenylphosphin)palladium (67 mg, 0.058 mmol) was added. The reaction mixture was refluxed overnight. The mixture was diluted with 100 mL acetonitrile and extracted three times with heptane (100 mL each). The acetonitrile phase was dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->80:20 gradient). The title compound was obtained as a yellow oil (544 mg, 64%), MS: m/e=291.3 (M+H+).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionextracted three times with heptane (100 mL each)
  3. dry with materialThe acetonitrile phase was dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->80:20 gradient)

Sources & evidence

ORD record
ord-999c8e150461410dae86b08e7d1e5638
Source dataset
uspto-grants-2011_08
Patent number
US07989628B2

Reaction notes

Loading…