Cesium carbonate → HCID 21071679, compound

HRID 1666855Notes

Reaction equation

HRID 1666855 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:28][CH2:29][CH2:30][CH3:31].CN1CCCC1=O>[Cl-].[Na+].O.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 10962Butyl iodideHCID 13387N-methyl-2-pyrrolidoneHCID 21071683HCID 21071683, compound

Product 1

HCID 21071679HCID 21071679, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Combine N-t-butoxycarbonyl-2-(6-hydroxy-1H-indol-3-yl)ethylamine (250 mg, 0.9 mmol), cesium carbonate (295 mg, 0.9 mmol) and 1-iodobutane (200 mg, 1.1 mmol) and N-methylpyrrolidinone (10 mL) and stir at ambient temperature for 2 hours and pour into 75 mL brine. Extract the mixture twice with 25 mL EtOAc. Wash the combined extracts with brine 2×50 mL, dry over MgSO4, and concentrate under vacuum to give an oil. Chromatograph the oil on silica gel eluting with 30% EtOAc in hexanes to give the title compound as a solid: ISMS 333 (M+1); Analysis for C19H28N2O3: calcd: C, 68.65; H, 8.49; N, 8.43. found: C, 68.83; H, 8.18; N, 8.33.

Workup

  1. extractionExtract the mixture twice with 25 mL EtOAc
  2. washWash the combined extracts with brine 2×50 mL
  3. dry with materialdry over MgSO4
  4. concentrationconcentrate under vacuum
  5. customto give an oil

Sources & evidence

ORD record
ord-4e9dca9f105b4da69b16489a8afd7aa4
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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