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Ethyl Acetate → N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-3-hydroxymethyl-N-methyl-5-trifluoromethyl-benzamide

HRID 878061
Notes
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Reaction equation

HRID 878061 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:26]=[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.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].CCOC(C)=O>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:29])([F:30])[F:28])[CH:26]=[C:4]([CH2:3][OH:2])[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 70663193N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-isophthalamic acid methyl ester

Product 1

HCID 70663287N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-3-hydroxymethyl-N-methyl-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-(2-chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-isophthalamic acid methyl ester (300 mg, 668 μmol, example 75) in THF (5 mL) was added LiAlH4 (26.6 mg, 702 μmol) at 0° C. The reaction mixture was stirred at this temperature for 1 hour. The reaction mixture was poured on 30 mL aqueous 10% potassium-sodium-tartrate solution and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc. The combined organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. 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 (102 mg, 36%). MS (ESI): m/z=421.092 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted a second time with 30 mL EtOAc
  3. washThe combined organic layers were washed with 30 mL brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  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-227199d30e2c44e1a52ed788abe28103
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