Water → HCID 71092430, compound

HRID 1529521Notes

Reaction equation

HRID 1529521 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][CH: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 71092430HCID 71092430, 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 hours. 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-2f9bd61335c8427998e7327e0ed0a91f
Source dataset
uspto-grants-2015_07
Patent number
US09090606B2

Reaction notes

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