Tributylstannane → HCID 57028617, compound

HRID 1741058Notes

Reaction equation

HRID 1741058 reaction equation
C([SnH](CCCC)CCCC)CCC.[C:14]([N:17]1[C:25]2[C:20](=[CH:21][C:22]([S:27][CH2:28][C:29]3[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH:34]=3)=[C:23](I)[CH:24]=2)[CH2:19][CH2:18]1)(=[O:16])[CH3:15].CC(N=NC(C#N)(C)C)(C#N)C.C(OCC)(=O)C>C1C=CC=CC=1>[C:14]([N:17]1[C:25]2[CH:24]=[C:23]3[C:29]4([CH2:28][S:27][C:22]3=[CH:21][C:20]=2[CH2:19][CH2:18]1)[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]4)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 8857Ethyl AcetateHCID 21833733HCID 21833733, compound

Product 1

HCID 57028617HCID 57028617, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of tributyltin hydride (0.251 ml, 0.934 mmol) in benzene (10 ml) was added dropwise over 30 minutes to a stirred solution of 1-acetyl-2,3-dihydro-6-iodo-5-[(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)methylthio]-1H-indole (D51) (0.200 g, 0.467 mmol) and AIBN (5 mg) in benzene (20 ml) under argon at reflux. Reflux was continued for a further 0.75 h. The reaction mixture was then allowed to cool. Ethyl acetate (10 ml) was then added and the mixture washed with 2.5M HCl (3×10 ml). The combined aqueous washings were then basified with solid potassium carbonate and the resultant suspension was extracted with dichloromethane (3×15 ml). The combined organic extracts were then dried (Na2SO4) and evaporated under reduced pressure to give a pale yellow solid which was dried in vacuo (0.127 g). The solid was purified by prep. TLC (15% MeOH/CH2Cl2 as eluant) to give the title compound as a cream solid (0.047 g, 33%).

Workup

  1. temperatureat reflux
  2. temperatureReflux
  3. temperatureto cool
  4. washthe mixture washed with 2.5M HCl (3×10 ml)
  5. extractionthe resultant suspension was extracted with dichloromethane (3×15 ml)
  6. dry with materialThe combined organic extracts were then dried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customto give a pale yellow solid which
  9. customwas dried in vacuo (0.127 g)
  10. customThe solid was purified by prep

Sources & evidence

ORD record
ord-d2a86a4d712f42a6a37c3bab446b6054
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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