Sodium Iodide → HCID 59191394, compound

HRID 1023978Notes

Reaction equation

HRID 1023978 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[CH:18]=[CH:17][C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[N:11]=2)=[C:7]([O:19][CH3:20])[CH:6]=1.[Na+].[I-].C(N(C(C)C)CC)(C)C.[NH:32]1[CH:36]=[N:35][CH:34]=[N:33]1>C1COCC1.CN(C=O)C>[F:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([O:9][C:8]2[CH:17]=[CH:18][C:5]([CH2:4][CH2:3][CH2:2][N:32]3[CH:36]=[N:35][CH:34]=[N:33]3)=[CH:6][C:7]=2[O:19][CH3:20])[N:11]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 92571H-1,2,4-TriazoleHCID 81531DiisopropylethylamineHCID 59191237HCID 59191237, compound

Product 1

HCID 59191394HCID 59191394, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-[4-(3-chloropropyl)-2-methoxyphenoxy]-6-fluoropyridine (0.14 mmol) in a THF/DMF mixture (340 μL/170 μL), under argon, was added NaI (0.14 mmol; 21 mg). The mixture was stirred 30 minutes at 50° C., before addition of diisopropylethylamine (0.28 mmol, 36 mg) and 1,2,4-triazol (0.28 mmol; 19 mg). The reaction mixture was allowed to stir overnight at 50° C. After concentration, the reaction was hydrolysed with saturated NH4Cl (1 mL), extracted with AcOEt (2*1 mL). Combined organic phases were dried over Na2SO4, concentrated in vacuo. The title compound (15 mg; 33%) was obtained as a yellow oil after purification on preparative TLC (dichloromethane/methanol: 9/1).

Workup

  1. concentrationAfter concentration
  2. extractionextracted with AcOEt (2*1 mL)
  3. dry with materialCombined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3561f0c46fb2494db9448604d2ad6914
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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