Water → HCID 69169795, compound

HRID 404918Notes

Reaction equation

HRID 404918 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].I[CH:12]([CH3:14])[CH3:13].O>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:12]([CH3:14])[CH3:13])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 27631086-Fluoropyridin-3-ol

Product 1

HCID 69169795HCID 69169795, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-fluoro-5-hydroxypyridine (6.000 g, 53.05 mmol) in N,N-dimethyl formamide (50 mL) cooled with an ice bath was added NaH (2.80 g, 60%, 70.0 mml) in several potions. After the addition, the mixture was stirred at 0° C. for 10 minutes. 2-iodopropane (6.5 mL, 65.00 mmol) was added. The mixture was stirred at room temperature for 2 hours. The mixture was poured into water, extracted with ether (2×), the combined extracts were washed with 1N NaOH (1×), water (1×), brine (1×), dried over MgSO4 and concentrated to give the product that was used directly without further purification.

Workup

  1. additionAfter the addition
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. extractionextracted with ether (2×)
  4. washthe combined extracts were washed with 1N NaOH (1×), water (1×), brine (1×)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give the product that
  8. customwas used directly without further purification

Sources & evidence

ORD record
ord-7b673fde5b36430dba30dfc1c5aeaa23
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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