2-(Tri-n-butylstannyl)thiophene → HCID 44351555, compound

HRID 1379558Notes

Reaction equation

HRID 1379558 reaction equation
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13](Br)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18].C([Sn](CCCC)(CCCC)[C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)CCC>C(#N)C>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13]([C:24]4[S:25][CH:26]=[CH:27][CH:28]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18]

Participants

4

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 15355317(4aR)-(10bR)-4,10b-dimethyl-8-bromo-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

Product 1

HCID 44351555HCID 44351555, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Five hundred mg of (4aR)-(10bR)-4,10b-dimethyl-8-bromo-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one was combined with 730 mg of 2-(tri-n-butylstannyl)thiophene and 100 mg of bis(triphenylphosphene)palladium chloride in 6 mL of acetonitrile in a screw capped sealable tube. The mixture was flushed with argon for 5 minutes, capped and heated at 90° for 20 h. Upon cooling, the mixture was filtered and the filtrate was concentrated in vacuum. The residue was purified by chromatography on a silica gel column, eluting with ethyl acetate, and the isolated product was recrystallized from ethyl acetate/hexane/chloroform to obtain 167 mg of the desired product. mp 193°-195°. FDMS 311.

Workup

  1. customcapped sealable tube
  2. customThe mixture was flushed with argon for 5 minutes
  3. customcapped
  4. temperatureheated at 90° for 20 h
  5. temperatureUpon cooling
  6. filtrationthe mixture was filtered
  7. concentrationthe filtrate was concentrated in vacuum
  8. customThe residue was purified by chromatography on a silica gel column
  9. washeluting with ethyl acetate
  10. customthe isolated product was recrystallized from ethyl acetate/hexane/chloroform

Sources & evidence

ORD record
ord-cb7e68de40eb4301bc911e2139d3caf1
Source dataset
uspto-grants-1997_09
Patent number
US05670514

Reaction notes

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