Sodium hydride → HCID 67485706, compound

HRID 1809587Notes

Reaction equation

HRID 1809587 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[Br:18])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([SH:27])[CH:24]=[CH:25][CH:26]=1.[H-].[Na+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:18][C:12]1[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=1[O:10][C:4]1[C:5]([C:8]#[N:9])=[N:6][CH:7]=[C:2]([S:27][C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([O:20][CH3:19])[CH:22]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 849893-MethoxybenzenethiolHCID 516892Sodium BicarbonateHCID 67485915HCID 67485915, compound

Product 1

HCID 67485706HCID 67485706, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL flask was charged with 5-bromo-3-(2-bromo-4-fluorophenoxy)picolinonitrile (10 g, 26.9 mmol), 3-methoxybenzenethiol (3.34 mL, 26.9 mmol), and DMF (250 mL). The reaction was cooled to 0° C. and NaH (0.710 g, 29.6 mmol) was added slowly. The reaction stirred for 30 minutes at 0° C. The reaction was poured into saturated aqueous sodium bicarbonate and extracted with EtOAc. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo to afford 3-(2-bromo-4-fluorophenoxy)-5-(3-methoxyphenylthio)picolinonitrile (12.0 g, 104% yield) as an amber oil.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c3fde1526c6445be83c2123e4b2b9ee7
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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