2-Fluoro-3-(tributylstannyl)pyridine → 3-(2-Fluoropyridin-3-yl)-2-(2-ethylaminopyridin-3-yl)thiophene

HRID 580823Notes

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 3-bromo-2-(2-ethylaminopyridin-3-yl)thiophene (0.085 g), 2-fluoro-3-tributylstannylpyridine (0.26 g) and Pd(Ph3P)2Cl2 (0.014 g) in N-methylpyrrolidinone (2 mL) was heated at 75° C. under argon for 1 day. The mixture was diluted with ethyl acetate, washed, dried, filtered and evaporated. The residue was chromatographed to give 3-(2-fluoropyridin-3-yl)-2-(2-ethylaminopyridin-3-yl)thiophene (0.028 g). mp 86-89° C.

Workup

washwashed
customdried
filtrationfiltered
customevaporated
customThe residue was chromatographed

Sources & evidence

ORD record: ord-400e687eb1fa41a78c0b0bd83bded3a1
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05919779

Reaction notes

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