Methyl iodide → HCID 86688974, compound

HRID 573308Notes

Reaction equation

HRID 573308 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]3[N:28]=[CH:27][CH:26]=[CH:25][C:19]=3[N:20]3[C:24]=2[CH2:23][CH2:22][CH2:21]3)=[CH:13][CH:12]=1.[C:29]([O-])([O-])=O.[K+].[K+].CI.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:29][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]3[N:28]=[CH:27][CH:26]=[CH:25][C:19]=3[N:20]3[C:24]=2[CH2:23][CH2:22][CH2:21]3)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 66728102HCID 66728102, compound

Product 1

HCID 86688974HCID 86688974, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 9-[4-(1H-benzimidazol-2-yloxy)phenyl]-7,8-dihydro-6H-pyrido[2,3-b]pyrrolizine (70 mg) and K2CO3 (79 mg) in DMF (1 mL) was added MeI (0.024 mL). The mixture was stirred at 40° C. overnight. The mixture was poured into saturated NaHCO3 aqueous solution and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (38.1 mg).

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-7eaf7fc990e24a94aeb8cf7d49a262d4
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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