Cesium carbonate → HCID 22121145, compound

HRID 1976816Notes

Reaction equation

HRID 1976816 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]4([CH2:17][CH2:18][C:5]=3[C:4]=2[CH:3]=1)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]4.C(=O)([O-])[O-:20].[Cs+].[Cs+].Br[CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:38])[CH3:37])=[CH:32][C:31]=1[O:39][CH3:40]>C(#N)C>[OH2:20].[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]4([CH2:17][CH2:18][C:5]=3[C:4]=2[CH:3]=1)[CH2:12][CH2:13][N:14]([CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:38])[CH3:37])=[CH:32][C:31]=1[O:39][CH3:40])[CH2:15][CH2:16]4

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 184039631-[4-(3-Bromopropoxy)-3-methoxyphenyl]ethan-1-oneHCID 18915247HCID 18915247, compound

Product 1

HCID 22121145HCID 22121145, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1,4-dihydro-7-fluorospiro[cyclopent[b]indole-3(2H), 4-piperidine] (3.00 g) in acetonitrile (30 ml) was added cesium carbonate (6.97 g) and 1-[4-(3-bromopropoxy)-3-methoxyphenyl]ethanone (3.38 g), under nitrogen, with stirring. The reaction mixture was heated at 80° C. for 3 hrs and allowed to cool to ambient temperature. The mixture was extracted with ethyl acetate. The extracts were washed with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was flashed chromatographed (silica gel) eluting with 1% acetone/dichloromethane. The appropriate fractions were collected and concentrated to give 1.00 g (30%) of product, mp 165-166° C.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extracts were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was flashed chromatographed (silica gel)
  8. washeluting with 1% acetone/dichloromethane
  9. customThe appropriate fractions were collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-0deba54947214cc9a1ee323c7f326d4e
Source dataset
uspto-grants-2001_05
Patent number
US06229014B1

Reaction notes

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