Methyl iodide → 6-(2,6-Diethyl-phenyl)-2-ethyl-4-methoxy-nicotinic acid methyl ester

HRID 251628Notes

Reaction equation

HRID 251628 reaction equation
[Li+].[CH3:2]C([N-]C(C)C)C.[CH3:9][O:10][C:11](=[O:31])[C:12]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([C:20]2[C:25]([CH2:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:28][CH3:29])=[N:14][C:13]=1[CH3:30].CI>>[CH3:9][O:10][C:11](=[O:31])[C:12]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([C:20]2[C:25]([CH2:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:28][CH3:29])=[N:14][C:13]=1[CH2:30][CH3:2]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 596783046-(2,6-Diethyl-phenyl)-4-methoxy-2-methyl-nicotinic acid methyl ester

Product 1

HCID 669935816-(2,6-Diethyl-phenyl)-2-ethyl-4-methoxy-nicotinic acid methyl ester

Conditions

Temperature
78 °C

Procedure

LDA (19 mg, 89 μL of 2 M solution in THF, 0.18 mmol) at −78° C. is added to a solution of 6-(2,6-diethyl-phenyl)-4-methoxy-2-methyl-nicotinic acid methyl ester (27 mg, 0.086 mmol). The mixture is stirred for 30 minutes at 78° C. Methyl iodide (15 μL, 0.24 mmol) is added and the resulting yellow mixture is stirred for 10 minutes at −78° C. After quenching with saturated NH4Cl the mixture is extracted with EtOAc. The combined extracts are dried, concentrated, and purified by flash-chromatography to give 6-(2,6-diethyl-phenyl)-2-ethyl-4-methoxy-nicotinic acid methyl ester.

Workup

  1. stirringthe resulting yellow mixture is stirred for 10 minutes at −78° C
  2. customAfter quenching with saturated NH4Cl the mixture
  3. extractionis extracted with EtOAc
  4. customThe combined extracts are dried
  5. concentrationconcentrated
  6. custompurified by flash-chromatography

Sources & evidence

ORD record
ord-42a4d830d8e74152a260482145deb644
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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