2-(Tri-n-butylstannyl)thiophene → HCID 15298022, compound

HRID 440768Notes

Reaction equation

HRID 440768 reaction equation
I[C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:29]1[S:30][CH:31]=[CH:32][CH:33]=1)CCC>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[S:30]1[CH:31]=[CH:32][CH:33]=[C:29]1[C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 15298021HCID 15298021, compound

Product 1

HCID 15298022HCID 15298022, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1.64 g of 10,11-dihydro-10-(4-iodobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 1.9 g of 2-tri-n-butylstannyl thiophene and 200 mg of tetrakis(triphenylphosphine)palladium(O) in 200 ml of toluene is refluxed under nitrogen for 16 hours. The reaction mixture is evaporated in vacuo to a residue which is purified by column chromatography on silica gel by elution with 5:1 hexane:ethyl acetate to give 1.2 g of the desired product as a solid. Mass spectrum: M+H:371.

Workup

  1. temperatureis refluxed under nitrogen for 16 hours
  2. customThe reaction mixture is evaporated in vacuo to a residue which
  3. customis purified by column chromatography on silica gel by elution with 5:1 hexane

Sources & evidence

ORD record
ord-3b68870837a24ce3b84652e929a7df35
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

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