Methyl iodide → HCID 44595604, compound

HRID 655364Notes

Reaction equation

HRID 655364 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH3:15])([CH3:14])[NH:12][C:11](=[O:16])[C:10]=2[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=3)=[CH:19][CH:18]=2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:37]I>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:13]([CH3:15])([CH3:14])[N:12]([CH3:37])[C:11](=[O:16])[C:10]=2[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=3)=[CH:19][CH:18]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 44594889HCID 44594889, compound

Product 1

HCID 44595604HCID 44595604, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-methoxyphenyl)-5,5-dimethyl-3-(4-(quinolin-2-ylmethoxy)phenyl)-1H-pyrrol-2(5H)-one (150 mg, 0.35 mmol) in DMF (10 mL) were added NaH (15 mg, 0.7 mmol) and CH3I (100 mg, 0.7 mmol) at 0° C. under an inert atmosphere. The mixture was then stirred for 4 h, diluted with cold water and filtered. The resulting residue was dried to afford 4-(4-methoxyphenyl)-1,5,5-trimethyl-3-(4-(quinolin-2-ylmethoxy)phenyl)-1H-pyrrol-2(5H)-one (50 mg, 37%) as a white solid. 1H NMR (500 MHz, d6-DMSO): δ 8.04 (d, J=7.2 Hz, 1H), 8.02-7.98 (m, 2H), 7.81-7.78 (m, 1H), 7.62-7.58 (m, 2H), 7.31-7.28 (m, 2H), 7.19-7.16 (m, 2H), 6.99-6.84 (m, 4H), 5.36 (s, 2H), 3.89 (s, 3H), 2.96 (s, 3H), 1.24 (s, 6H). MS: M+H: m/z=465.2; M+Na: m/z=487.2. HPLC: 92%, (Condition-I).

Workup

  1. filtrationfiltered
  2. customThe resulting residue was dried

Sources & evidence

ORD record
ord-63834a2a47124e2791c34fc4b332cf6c
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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