2-(Tributylstannyl)pyridine → HCID 10990326, compound

HRID 1385290Notes

Reaction equation

HRID 1385290 reaction equation
Br[C:2]1[S:3][C:4]([S:14][CH3:15])=[C:5]2[C:10](=[O:11])[CH2:9][C:8]([CH3:13])([CH3:12])[CH2:7][C:6]=12.C([Sn](CCCC)(CCCC)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)CCC>O1CCOCC1>[CH3:12][C:8]1([CH3:13])[CH2:7][C:6]2=[C:2]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[S:3][C:4]([S:14][CH3:15])=[C:5]2[C:10](=[O:11])[CH2:9]1

Participants

4

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 2820226HCID 2820226, compound

Product 1

HCID 10990326HCID 10990326, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Bromo-6,6-dimethyl-3-methylthio-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (300 mg, 1 mmol) was dissolved in dioxane (25 mL), and 2-(tri-n-butylstannyl)pyridine (550 mg, 1.35 mmol) was added. The solution was degassed with nitrogen then tetrakis (tri-phenylphosphine)palladium (30 mg, 0.025 mmol) was added and the solution refluxed for 16 h. The solvent was then removed in vacuo and the residue triturated with a mixture of ethyl acetate and hexane (1:3). After filtration the solid product was washed with a little diethyl ether to give the title compound as a white solid (170 mg, 57%). mp 217-220° C. Found: C, 63.02; H, 5.64; N, 4.47%. C16H17NOS2 requires; C, 63.36; H, 5.61; N, 4.62%. 1HNMR (250 MHz, CDCl3)δ 1.08 (6H, s), 2.44 (2H, s), 2.65 (3H, s), 2.93 (2H, s), 7.18 (1H, m), 7.47 (1H, d, J=8 Hz), 7.71-7.77 (1H, m), 8.61-8.63 (1H, m). MS (ES+) 304 (M+1).

Workup

  1. customThe solution was degassed with nitrogen
  2. temperaturethe solution refluxed for 16 h
  3. customThe solvent was then removed in vacuo
  4. customthe residue triturated with a mixture of ethyl acetate and hexane (1:3)
  5. filtrationAfter filtration the solid product
  6. washwas washed with a little diethyl ether

Sources & evidence

ORD record
ord-e0c80c119acd450197879e646da03c0a
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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