Hydrochloric Acid → 5-(6-Bromo-pyridine-3-carbonyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one

HRID 532629Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:9])[CH2:7][CH2:8][C:2]1=2.[H-].[Na+].C([O:14][C:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[N:18][CH:17]=1)C.Cl>C1COCC1.C(OCC)(=O)C.O>[Br:22][C:19]1[N:18]=[CH:17][C:16]([C:15]([CH:7]2[CH2:8][C:2]3[S:1][CH:5]=[CH:4][C:3]=3[C:6]2=[O:9])=[O:14])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

5,6-Dihydro-cyclopenta[b]thiophen-4-one (1.38 g, 10 mmol) in 30 mL of THF was treated with NaH (60 percent, 0.6 g, 15 mmol). After the addition of 6-Bromo-nicotinic acid ethyl ester (2.3 g, 10 mmol), the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (80 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(6-Bromo-pyridine-3-carbonyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (2.28 g, 7.1 mmol) as red solid in 71% yield.

Workup

temperatureThe solution was cooled to room temperature
customThe organic layer was collected
dry with materialdried over MgSO4(s)
concentrationconcentrated under reduced pressure
customThe resultant precipitate was collected
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-41ad21f00f064b18b3f7c70276f10a2e
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853207B2

Reaction notes

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