2-(Tri-n-butylstannyl)thiophene → Methyl 6-thien-2-ylnicotinate

HRID 440765

Reaction equation

HRID 440765 reaction equation
O[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)CCC>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.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:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 178498304HCID 178498304, compound

Product 1

HCID 17879034Methyl 6-thien-2-ylnicotinate

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2.0 g of (methyl 6-hydroxypyridine-3-carboxylate, o-triflate) and 5.23 g of 2-(tributylstannyl)thiophene in 50 ml of dry toluene is stirred under nitrogen at reflux for 16 hours in the presence of tetrakis(triphenylphosphine)palladium(O). The reaction mixture is diluted with 50 ml of chloroform and filtered through a pad of diatomaceous earth. The filtrate is evaporated in vacuo to a residue which is extracted and decanted (2×100 ml) with 1:1 ether:petroleum ether. The combined extracts are evaporated in vacuo to give 1.6 g of the desired product as a residue.

Workup

  1. filtrationfiltered through a pad of diatomaceous earth
  2. customThe filtrate is evaporated in vacuo to a residue which
  3. extractionis extracted
  4. customdecanted (2×100 ml) with 1:1 ether
  5. customThe combined extracts are evaporated in vacuo

Sources & evidence

ORD record
ord-3023e0090bc042f38e9eb76b5d347720
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Linked notes

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