Dimethylformamide → HCID 69218892, compound

HRID 1394618Notes

Reaction equation

HRID 1394618 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][C:9]([CH:15]([CH3:17])[CH3:16])=[CH:8][C:7]=1[C:18]1[C:26]2C(=[CH:22][CH:23]=[C:24]([C:27]([CH3:32])=[CH:28]C(O)=O)[CH:25]=2)NC=1)[CH2:2][CH2:3][CH3:4].[C:33](=[O:36])([O-])[O-:34].[Cs+].[Cs+].I[CH3:40].[CH3:41][N:42]([CH:44]=O)[CH3:43]>O>[CH3:40][O:34][C:33](=[O:36])[CH:28]=[C:27]([C:24]1[CH:25]=[C:26]2[C:43](=[CH:22][CH:23]=1)[N:42]([CH3:41])[CH:44]=[C:18]2[C:7]1[CH:8]=[C:9]([CH:15]([CH3:17])[CH3:16])[CH:10]=[C:11]([CH:12]([CH3:13])[CH3:14])[C:6]=1[O:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH3:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 66899696HCID 66899696, compound

Product 1

HCID 69218892HCID 69218892, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

3-[3-(2-Butoxy-3,5-diisopropyl-phenyl)-1H-indol-5-yl]-but-2-enoic acid (129 mg, 0.30 mmol), cesium carbonate (293 mg, 0.90 mmol), and iodomethane (0.041 mL, 65 mmol) were combined in DMF (6 mL) and heated at 40° C. for 2 h. The reaction was diluted with water and extracted with ethyl acetate (2×). The organic portions were combined and washed with brine, dried (MgSO4), filtered and concentrated in vacuo to provide 139 mg of a yellow oil. The material was purified using radial chromatography by elution with (95:5) hexane:ethyl acetate to provide 119 mg (86%) of product.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-30d19c70cb7b4d46a3ea47b06644e66b
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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