Sodium Carbonate → 3-(benzyloxy)-1-(3-iodopropyl)pyridin-2(1H)-one

HRID 1909481

Reaction equation

HRID 1909481 reaction equation
[I:1][CH2:2][CH2:3][CH2:4]I.[CH2:6]([O:13][C:14]1[C:15](=[O:20])[NH:16][CH:17]=[CH:18][CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[CH2:6]([O:13][C:14]1[C:15](=[O:20])[N:16]([CH2:4][CH2:3][CH2:2][I:1])[CH:17]=[CH:18][CH:19]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123141,3-DiiodopropaneHCID 156664523-(Benzyloxy)pyridin-2-ol

Product 1

HCID 595371893-(benzyloxy)-1-(3-iodopropyl)pyridin-2(1H)-oneYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1,3-diiodopropane (7.1 mL, 63 mmol) in tetrahydrofuran (50 mL) was added 3-(benzyloxy)pyridin-2(1H)-one (1.28 g, 6.3 mmol) and Na2CO3 (0.67 g, 6.3 mmol). The mixture was then stirred at 70° C. for 1 day. Reaction progress was monitored by ES-MS. After ESMS showed essentially complete consumption of the starting material 3-(benzyloxy)pyridin-2(1H)-one, the reaction was stopped. Then the reaction mixture was filtered, concentrated, and subjected to flash column chromatography (eluent: hexane:ethylacetate 1:1). Compound 7 was obtained (240 mg, 10% yield). Analysis: ES-MS (positive ion in MeOH/H2O): m/z=370.2, ([M+H]+, calculated: 370.03).

Workup

  1. customReaction progress
  2. customconsumption of the starting material 3-(benzyloxy)pyridin-2(1H)-one
  3. filtrationThen the reaction mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8ed2954d6a1a413c8a84075910a87a2c
Source dataset
uspto-grants-2013_12
Patent number
US08598381B2

Linked notes

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