Isobutyl iodide → HCID 66571466, compound

HRID 83643Notes

Reaction equation

HRID 83643 reaction equation
[CH2:1]([N:8]([CH3:28])[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:32][CH:33]([CH3:35])[CH3:34]>CN(C=O)C.O.C(OCC)(=O)C>[CH2:1]([N:8]([CH3:28])[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[N:20]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10556Isobutyl iodideHCID 24758Sodium hydrideHCID 66571403N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide

Product 1

HCID 66571466HCID 66571466, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide (100 mg, 0.266 mmol) was dissolved in 1.0 mL of DMF and added to a suspension of sodium hydride (12.78 mg, 0.320 mmol) in 2.0 mL of DMF. The reaction was stirred at 80° C. for 10 minutes before adding 1-iodo-2-methylpropane (0.061 mL, 0.533 mmol). The reaction was allowed to stir overnight. After 18 hours, the reaction was cooled to room temperature before diluting with water and ethyl acetate. The organic phase was washed with water followed by saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated. The crude material was purified via column chromatography using 50% ethyl acetate/hexanes to 100% ethyl acetate. The purification provided product as a white solid. (Yield: 28 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 7.64-7.51, 7.43-7.16, 7.11-7.03, 6.71-6.61, 4.67, 4.51, 4.19-4.07, 3.13-2.91, 2.79, 2.06-1.93, 1.88-1.50, 0.84-0.73

Workup

  1. stirringto stir overnight
  2. waitAfter 18 hours
  3. temperaturethe reaction was cooled to room temperature
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified via column chromatography
  9. customThe purification
  10. customprovided product as a white solid

Sources & evidence

ORD record
ord-66bfe81d4dcb410daaba05483a497893
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

Loading…