Iodoethane → HCID 70655560, compound

HRID 705209Notes

Reaction equation

HRID 705209 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[N:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][C:12]=1[F:21].[H-].[Na+].[CH2:24](I)[CH3:25]>CN(C=O)C>[CH2:24]([O:9][CH2:8][C:6]1[CH:5]=[C:4]([F:10])[C:3]([C:11]2[N:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][C:12]=2[F:21])=[C:2]([F:1])[CH:7]=1)[CH3:25]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydride2×HCID 70654789HCID 70654789, compound

Product 1

HCID 70655560HCID 70655560, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 6-(2,6-difluoro-4-(hydroxymethyl)phenyl)-5-fluoropicolinate (1.0 equiv.) in DMF (0.20 M) (colorless) at 0° C. was added sodium hydride (1.2 equiv.) and the reaction was stirred at 0° C. for 2 min. Ethyl iodide (1.2 equiv.) was added and the reaction was allowed to warm to room temperature. After 1 h, additional 1.0 equiv. of NaH was added and stirred for 15 mi. Reaction was quenched by the addition of sat. Ammonium chloride. The aqueous was acidified with conc HCl to pH3 and extracted with ethyl acetate three times. The organics were combined, dried with MgSO4, filtered and concentrated. The crude mixture was used as is. LC/MS=326.0 (MH+), Rt=0.94 min.

Workup

  1. temperatureto warm to room temperature
  2. waitAfter 1 h
  3. stirringstirred for 15 mi
  4. customReaction
  5. customwas quenched by the addition of sat. Ammonium chloride
  6. extractionextracted with ethyl acetate three times
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8c2ce88e40fa418b98810317559e0bf6
Source dataset
uspto-grants-2015_11
Patent number
US09173883B2

Reaction notes

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