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Water → 6-chloro-2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-pyridine-3-carboxylic acid amide

HRID 1753852
Notes
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Reaction equation

HRID 1753852 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14](F)[CH:13]=2)=[O:9])=[C:6]([CH3:20])[CH:5]=[C:4]([Cl:21])[N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:28]([SH:30])[CH3:29].O>CN(C=O)C>[Cl:21][C:4]1[N:3]=[C:2]([S:30][CH2:28][CH3:29])[C:7]([C:8]([NH:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([F:18])[CH:17]=2)=[O:9])=[C:6]([CH3:20])[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 866643152,6-dichloro-N-(3,5-difluorobenzyl)-4-methyl-pyridine-3-carboxylic acid amide

Product 1

HCID 866643146-chloro-2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-pyridine-3-carboxylic acid amideYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4.0 g (12.8 mmol) 2,6-dichloro-N-(3,5-difluorobenzyl)-4-methyl-pyridine-3-carboxylic acid amide in DMF (30 ml) was treated with 2.6 g (19.2 mmol) K2CO3 and 1.2 ml (16.0 mmol) ethanethiol, followed by stirring in a closed vessel at RT for 16 h. Then water (35 ml) was added and the mixture was extracted with EtOAc (2×70 ml). The combined organic layers were washed with water, a 2M aq. NaOH sol. and brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 3:1) provided 3.3 g (9.7 mmol, 76%) 6-chloro-2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-pyridine-3-carboxylic acid amide.

Workup

  1. extractionthe mixture was extracted with EtOAc (2×70 ml)
  2. washThe combined organic layers were washed with water
  3. dry with materiala 2M aq. NaOH sol. and brine, dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by CC (hexane/EtOAc 3:1)

Sources & evidence

ORD record
ord-70991bde56d841b285b4b9ff43e3f8dc
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09168259B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes