Cesium carbonate → HCID 68827000, compound

HRID 2361372Notes

Reaction equation

HRID 2361372 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[NH:8]2)=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][O:18][CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH3:19][O:18][CH2:17][CH2:16][O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 10535709methyl 6-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 68827000HCID 68827000, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To a light brown, homogeneous solution of methyl 6-hydroxy-1H-indole-2-carboxylate (1.4862 g, 7.77 mmol) and 1-bromo-2-methoxyethane (0.731 mL, 7.77 mmol) in DMF (38.9 mL) under nitrogen was added cesium carbonate (2.53 g, 7.77 mmol). The reaction was heated to 55° C. and stirred overnight. The reaction was cooled to room temperature, diluted with EtOAc (200 mL) and filtered through CELITE®. The filtrate was washed with water (4×50 mL) and brine (2×50 mL), dried over MgSO4, and concentrated in vacuo to give a residue which was purified by flash chromatography using an ISCO 120 g column eluting with 20-60% EtOAc/hexanes. Appropriate fractions were collected and concentrated in vacuo to give desired product (0.8592 g) as a white solid. Mixed fractions were combined and concentrated in vacuo to give a residue which was purified by flash chromatography using an ISCO 80 g column eluting with 20-60% EtOAc/hexanes to give another crop of desired product (0.1673 g) as a white solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered through CELITE®
  3. washThe filtrate was washed with water (4×50 mL) and brine (2×50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a residue which
  7. customwas purified by flash chromatography
  8. washeluting with 20-60% EtOAc/hexanes
  9. customAppropriate fractions were collected
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1754ad6f7f174d5685ab783f7d50cebd
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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