Methyl iodide → 2-(2-Cyclopropyl-5-(methoxycarbonyl)-4-methylphenyl)-5-methyl-3H-imidazo[4,5-c]pyridin-5-ium iodide

HRID 1487971Notes

Reaction equation

HRID 1487971 reaction equation
[CH:1]1([C:4]2[C:13]([C:14]3[NH:22][C:17]4[CH:18]=[N:19][CH:20]=[CH:21][C:16]=4[N:15]=3)=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:23])[CH:5]=2)[CH2:3][CH2:2]1.[I:24][CH3:25]>ClCCl>[I-:24].[CH:1]1([C:4]2[CH:5]=[C:6]([CH3:23])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][C:13]=2[C:14]2[NH:22][C:17]3[CH:18]=[N+:19]([CH3:25])[CH:20]=[CH:21][C:16]=3[N:15]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 90021751Methyl 4-cyclopropyl-5-(3H-imidazo[4,5-c]pyridin-2-yl)-2-methylbenzoate2×

Product 1

HCID 900303632-(2-Cyclopropyl-5-(methoxycarbonyl)-4-methylphenyl)-5-methyl-3H-imidazo[4,5-c]pyridin-5-ium iodideYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of methyl 4-cyclopropyl-5-(3H-imidazo[4,5-c]pyridin-2-yl)-2-methylbenzoate (compound 87.2, 500 mg, 1.63 mmol) in dichloromethane (15 mL). Iodomethane (203 μL, 3.26 mmol) was added drop-wise and the resulting solution was stirred overnight at room temperature. The mixture was concentrated under reduced pressure to yield 0.30 g (41%) of the title compound as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f34863186b8d498ead846df8e351d0e1
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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