Tributylvinyltin → HCID 68574383, compound

HRID 1949004Notes

Reaction equation

HRID 1949004 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])[CH:6]=[CH:5]2.[CH:22]([Sn](CCCC)(CCCC)CCCC)=[CH2:23]>C1(C)C=CC=CC=1>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:22]=[CH2:23])[CH:3]=2)[N:8]=1

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 68574436HCID 68574436, compound

Product 1

HCID 68574383HCID 68574383, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(6-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (example 2, step A, 500 mg, 1.46 mmol) was dissolved in 20 mL toluene. The reaction mixture was evacuated and backfilled with argon for three times to remove oxygen. Vinyltributyltin (462 mg, 1.46 mmol) and tetrakis(triphenylphosphin)palladium(0) (34 mg, 0.029 mmol) were added. The reaction mixture was refluxed overnight and evaporated. The residue was poured into 50 mL acetonitrile and extracted three times with heptane (50 mL each) to remove the tin products. The acetonitrile phase was dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient). (2-Methoxy-benzyl)-(6-vinyl-quinolin-2-yl)-amine was obtained as a yellow oil (478 mg), MS: m/e=291.1 (M+H+).

Workup

  1. customThe reaction mixture was evacuated
  2. customto remove oxygen
  3. temperatureThe reaction mixture was refluxed overnight
  4. customevaporated
  5. additionThe residue was poured into 50 mL acetonitrile
  6. extractionextracted three times with heptane (50 mL each)
  7. customto remove the tin products
  8. dry with materialThe acetonitrile phase was dried with sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient)

Sources & evidence

ORD record
ord-742921a5ddef4a639ddd313a2361ec43
Source dataset
uspto-grants-2013_03
Patent number
US08399674B2

Reaction notes

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