Triethylamine → 2-Dimethylaminomethyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester

HRID 1242372Notes

Reaction equation

HRID 1242372 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:6][C:5]=1[CH2:20]Br.Cl.[CH3:24][NH:25][CH3:26].C(N(CC)CC)C>C(#N)C>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:6][C:5]=1[CH2:20][N:25]([CH3:26])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 67072139HCID 67072139, compound

Product 1

HCID 670721832-Dimethylaminomethyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.102 g (0.273 mmol) of the above (example 45A]) prepared 2-bromomethyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester was dissolved in 1.5 ml of acetonitrile and treated with 0.027 g (0.331 mmol) of dimethylamine hydrochloride and 0.080 ml (2 eq.) of triethylamine. After stirring for 2 h at ambient temperature, the reaction mixture was poured onto crashed ice/KHSO4-solution and extracted twice with AcOEt. Washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, AcOEt/MeOH/NEt3=9/1/0.05), produced 0.047 g of pure title compound as off-white crystals.

Workup

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with AcOEt
  3. washWashing with water and brine
  4. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-6b417a8272c64b3995594d1a145786bf
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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