Sodium Iodide → HCID 59652003, compound

HRID 221831Notes

Reaction equation

HRID 221831 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:15])[NH:13][N:14]=2)=[CH:5][CH:4]=1.Br[CH2:17][CH2:18][F:19].[Na+].[I-].C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N>[F:19][CH2:18][CH2:17][N:13]1[C:12](=[O:15])[CH:11]=[CH:10][C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:14]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 129822-Fluoroethyl bromideHCID 28101666-(4-Methoxyphenyl)-2,3-dihydropyridazin-3-one

Product 1

HCID 59652003HCID 59652003, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6-(4-methoxyphenyl)-2H-pyridazin-3-one (170 mg, 0.83 mmol), 1-bromo-2-fluoroethane (122.5 mg, 1.5 eq.), NaI (20 mg) and cesium carbonate (553 mg, 2.0 eq.) in 5 mL of CH3CN was heated to 70° C. overnight. The reaction mixture was filtered and concentrated. The product was purified by ISCO combiflash with 50% hexane and EtOAc to give 2-(2-fluoroethyl)-6-(4-methoxyphenyl)-2H-pyridazin-3-one (200 mg, 97%); MS m/z 349 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe product was purified by ISCO combiflash with 50% hexane and EtOAc

Sources & evidence

ORD record
ord-d39faffa1678493c8c083c9712e16ab1
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Reaction notes

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