Methyl iodide → HCID 67339781, compound

HRID 1675076Notes

Reaction equation

HRID 1675076 reaction equation
IC.[C:3]([O:7][C:8]([N:10]1[CH2:15][CH:14]=[C:13]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]([OH:27])=[O:26])[CH:23]=3)[NH:18][CH:17]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:28](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH:12]=[C:13]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[CH:23]=3)[NH:18][CH:17]=2)[CH2:14][CH2:15]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67341449HCID 67341449, compound

Product 1

HCID 67339781HCID 67339781, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (1.22 mL, 19.63 mmol) was added in one portion to 3-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole-5-carboxylic acid (6.72 g, 19.63 mmol) and potassium carbonate (3.26 g, 23.55 mmol) in DMF (60 mL) at ambient temperature. The resulting mixture was stirred at ambient temperature for 3 hours then quenched in water (200 mL) and extracted with MTBE (2×100 mL). The extract was washed sequentially with water (3×100 mL) and saturated brine, dried over MgSO4 and concentrated by evaporation then purified by flash silica chromatography, elution gradient 20 to 35% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 3-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole-5-carboxylate (5.09 g, 73%) as a colourless solid.

Workup

  1. customthen quenched in water (200 mL)
  2. extractionextracted with MTBE (2×100 mL)
  3. washThe extract was washed sequentially with water (3×100 mL) and saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated by evaporation
  6. customthen purified by flash silica chromatography, elution gradient 20 to 35% EtOAc in isohexane
  7. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-d49589ba2a5a4fb2a2214051e6dcfe39
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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