Tetrabutylammonium Fluoride → 3-(2-Fluoropyridin-3-yl)-4-(2-ethylaminopyridin-3-yl)thiophene

HRID 580816Notes

Reaction equation

HRID 580816 reaction equation
Br[C:2]1[C:6]([C:7]2[C:8]([NH:13][CH2:14][CH3:15])=[N:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][S:4][CH:3]=1.[F:16][C:17]1[C:22]([Sn](CCCC)(CCCC)CCCC)=[CH:21][CH:20]=[CH:19][N:18]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>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>[F:16][C:17]1[C:22]([C:2]2[C:6]([C:7]3[C:8]([NH:13][CH2:14][CH3:15])=[N:9][CH:10]=[CH:11][CH:12]=3)=[CH:5][S:4][CH:3]=2)=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

7

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 110903192-Fluoro-3-(tributylstannyl)pyridineHCID 154085623-Bromo-4-(2-ethylaminopyridin-3-yl)thiophene

Product 1

HCID 154085633-(2-Fluoropyridin-3-yl)-4-(2-ethylaminopyridin-3-yl)thiopheneYield 23.5%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-4-(2-ethylaminopyridin-3-yl)thiophene (0.31 g), 2-fluoro-3-tributylstannylpyridine (0.507 g) and Pd(Ph3P)2Cl2 (0.035 g) in N-methylpyrrolidinone (3 mL), in a sealed tube, was heated at 100° C. for 17 hours. The mixture was cooled and tetrabutylammonium fluoride (1M in tetrahydrofuran, 1 mL) was added. After one day, the mixture was diluted with ethyl acetate, washed with water, dried, filtered, and evaporated. The residue was fractionated by chromatography to give 3-(2-fluoropyridin-3-yl)-4-(2-ethylaminopyridin-3-yl)thiophene (0.077 g) mp 127-129° C.

Workup

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

Sources & evidence

ORD record
ord-2b89e96d512f474c823763dab6484268
Source dataset
uspto-grants-1999_07
Patent number
US05919779

Reaction notes

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