Potassium Carbonate → Ethyl 6-iodo-1-(2-(1-methylpiperidin-4-yl)ethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2061862Notes

Reaction equation

C[N:2]([CH3:20])/[CH:3]=[C:4](/[C:10](=[O:19])[C:11]1[CH:16]=[C:15]([I:17])[CH:14]=[CH:13][C:12]=1F)\[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:21][N:22]1[CH2:27][CH2:26][CH:25]([CH:28](N)C)[CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[I:17][C:15]1[CH:16]=[C:11]2[C:12](=[CH:13][CH:14]=1)[N:2]([CH2:20][CH2:28][CH:25]1[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]1)[CH:3]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:10]2=[O:19]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate (Intermediate 24, 1 g, 2.56 mmol) dissolved in THF (5.5 mL) was added 2-(1-methylpiperidin-4-yl-ethanamine (0.406 mL, 2.56 mmol). The reaction mixture was stirred at 60° C. for 2 h. Potassium carbonate was added (1.06 g, 7.67 mmol), and the reaction was stirred for 18 h and cooled down to room temperature. The reaction was quenched with 1 N HCl and partitioned between dichloromethane (10 mL) and water (20 mL). The aqueous layer was extracted with dichloromethane (2×10 mL), and the organics were dried over sodium sulfate and concentrated to give ethyl 6-iodo-1-(2-(1-methylpiperidin-4-yl)ethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate as a light yellow solid (1.08 g, 90%).

Workup

stirringthe reaction was stirred for 18 h
temperaturecooled down to room temperature
customThe reaction was quenched with 1 N HCl
custompartitioned between dichloromethane (10 mL) and water (20 mL)
extractionThe aqueous layer was extracted with dichloromethane (2×10 mL)
dry with materialthe organics were dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-2083f98bfad14022a2943af58faadc32
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283361B2

Reaction notes

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