3,4-Dibromothiophene → 3-Bromo-4-(2-fluoropyridin-3-yl)thiophene

HRID 580814Notes

Reaction equation

HRID 580814 reaction equation
[F:1][C:2]1[C:7]([Sn](CCCC)(CCCC)CCCC)=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:21][C:22]1[C:26](Br)=[CH:25][S:24][CH:23]=1.[F-].[K+]>CN1CCCC1=O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:21][C:22]1[C:26]([C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:25][S:24][CH:23]=1

Participants

7

Reactant 3

HCID 184523,4-DibromothiopheneHCID 522689Potassium FluorideHCID 110903192-Fluoro-3-(tributylstannyl)pyridine

Product 1

HCID 154085613-Bromo-4-(2-fluoropyridin-3-yl)thiopheneYield 27.6%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-fluoro-3-tributylstannylpyridine (1.9 g), 3, 4-dibromothiophene (1.5 g) and Pd(Ph3P)2Cl2 (0.175 g) in N-methylpyrrolidinone (7.5 mL), in a sealed tube, was heated at 100° C. for 16 hours. The mixture was cooled and stirred with aqueous potassium fluoride for 6 hours. The mixture was diluted with ethyl acetate, washed with water, dried filtered and evaporated. The residue was fractionated by chromatography to give 3-bromo-4-(2-fluoropyridin-3-yl)thiophene (0.35 g), mp 48-50° C.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-83eae3fdba584131b316cfdaea36b509
Source dataset
uspto-grants-1999_07
Patent number
US05919779

Reaction notes

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