Indole → HCID 25051885, compound

HRID 1157989Notes

Reaction equation

HRID 1157989 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Cl[CH2:13][C:14]([NH:16][CH2:17][CH2:18][N:19]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH3:20])=[O:15]>CN(C=O)C.CCOC(C)=O>[CH:21]1([N:19]([CH3:20])[CH2:18][CH2:17][NH:16][C:14](=[O:15])[CH2:13][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 798IndoleHCID 24758Sodium hydrideHCID 59014368HCID 59014368, compound

Product 1

HCID 25051885HCID 25051885, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Indole (20 mg, 0.17 mmol) was dissolved in DMF (400 μL) and NaH (60% dispersed in mineral oil, 9 mg, 0.22 mmol) was added and the resultant mixture was stirred at 60° C. for 30 minutes. The mixture was then cooled to room temperature to it was added crude chloride 2a (˜50 mg; excess). The reaction solution was then heated to 60° C. for 2 hours. The reaction solution was cooled to room temperature and diluted in EtOAc and the organic solution was washed with H2O (2×) and brine (1×). The organic layer was dried (MgSO4) and concentrated to provide crude 3a which was purified by preparative TLC (2:1:0.4 EtOAc/hexanes/Et3N) to give the desired product 3a (7 mg, 13% yield): LC-MS (Method B, retention time=0.448 min. MS calc'd for C19H28N3O (MH+): 314.2. Found 314.5.

Workup

  1. temperatureThe reaction solution was then heated to 60° C. for 2 hours
  2. temperatureThe reaction solution was cooled to room temperature
  3. washthe organic solution was washed with H2O (2×) and brine (1×)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0a8d90afb4b848f1adf13854bca583ce
Source dataset
uspto-grants-2010_10
Patent number
US07807704B2

Reaction notes

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