Methyl iodide → HCID 178496644, compound

HRID 1486929Notes

Reaction equation

HRID 1486929 reaction equation
[CH3:1]I.[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[N:10]=[CH:9][C:8]3[NH:14][C:15](=[O:23])[N:16]([C@H:17]4[CH2:20][C@@H:19]([O:21][CH3:22])[CH2:18]4)[C:7]=3[C:6]=2[CH:5]=1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[N:10]=[CH:9][C:8]3[N:14]([CH3:1])[C:15](=[O:23])[N:16]([C@H:17]4[CH2:18][C@@H:19]([O:21][CH3:22])[CH2:20]4)[C:7]=3[C:6]=2[CH:5]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178496648HCID 178496648, compound

Product 1

HCID 178496644HCID 178496644, compoundYield 75.1%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl iodide (11.49 mL, 183.81 mmol) was added to a mixture of 8-bromo-1-(cis-3-methoxycyclobutyl)-3H-imidazo[4,5-c]quinolin-2-one (32 g, 91.90 mmol), sodium hydroxide (5.51 g, 137.85 mmol) and tetrabutylammonium bromide (2.94 g, 9.19 mmol) in DCM (400 mL) and water (300 mL) and the resulting mixture stirred at r.t. for 2 h. The DCM was removed in vacuo and the precipitate collected by filtration, washed with water (200 mL) and dried under vacuum to afford the desired material (25.00 g, 75%) as a pale yellow solid. NMR Spectrum: 1H NMR (400 MHz, DMSO-d6) δ 2.72-2.86 (2H, m), 2.9-3.08 (2H, m), 3.22 (3H, s), 3.49 (3H, s), 3.85-3.89 (1H, m), 4.88-5.06 (1H, m), 7.74 (1H, dd), 7.98 (1H, d), 8.50 (1H, d), 8.92 (1H, s). Mass Spectrum: m/z (ES+)[M+H]+=362, 364.

Workup

  1. customThe DCM was removed in vacuo
  2. filtrationthe precipitate collected by filtration
  3. washwashed with water (200 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-25a390e680a4481fbb530a5d5bef85dc
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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