Water → HCID 71092428, compound

HRID 2279924Notes

Reaction equation

HRID 2279924 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:23])[CH:5]=[C:6]([Cl:22])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([OH:21])[CH:12]=1)[OH:10].[C:24]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[Cl:22][C:6]1[CH:5]=[N+:4]([O-:23])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH3:24])[CH:12]=1)[OH:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86720686HCID 86720686, compound

Product 1

HCID 71092428HCID 71092428, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-3,5-Dichloro-4-(2-(4-(difluoromethoxy)-3-hydroxyphenyl)-2-hydroxyethyl)pyridine 1-oxide (2 g, 5.46 mmol) was dissolved in DMF (16 mL) then K2CO3 (2 g, 14.47 mmol) and iodomethane (1.72 g, 12.12 mmol) were added and the mixture was stirred at r.t. for 4 h. The mixture was poured into 200 mL of water, filtered, washed with water and dried under vacuum at 40° C. 1.98 g of whitish solid was obtained.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. customdried under vacuum at 40° C

Sources & evidence

ORD record
ord-f9335c402ec74203acb191c8fbcfc8d0
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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