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Potassium sodium tartarate → N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-3-(1-hydroxy-1-methyl-ethyl)-N-methyl-5-trifluoromethyl-benzamide

HRID 878062
Notes
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Reaction equation

HRID 878062 reaction equation
COC(=O)C1C=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:6]([C:7]([N:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[CH3:10])=[O:8])[CH:5]=1.[CH3:32][Mg]Br.[C:35]([CH:38]([CH:40]([C:42]([O-])=O)O)[OH:39])([O-])=O.[K+].[Na+]>C1COCC1>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[N:9]([CH3:10])[C:7](=[O:8])[C:6]1[CH:24]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:42]=[C:40]([C:38]([OH:39])([CH3:35])[CH3:32])[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 70663193N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-isophthalamic acid methyl esterHCID 178418573HCID 178418573, compound

Product 1

HCID 70663326N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-3-(1-hydroxy-1-methyl-ethyl)-N-methyl-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of N-[4-(2-chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-isophthalamic acid methyl ester (200 mg, 446 μM, example 75) in THF (3.3 mL) were added methyl magnesium bromide (1M solution in butyl ether, 1.6 mL, 1.56 mmol) within 2 min. The reaction was poured on EtOAc (20 mL) and aqueous sodium potassium tartrate solution (20 mL) and the phases were separated. The aqueous phase was extracted with EtOAc (20 mL) and the combined organic phases were washed with brine, dried over magnesium sulfate, filtered and evaporated. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless solid (115 mg, 57%). MS (ESI): m/z=449.123 [M+H]+.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with EtOAc (20 mL)
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe compound was purified by silica gel chromatography
  8. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-ac7b7b39acd9477db4e05fea79256d15
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987307B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes