Borane;tetrahydrofuran → HCID 22627226, compound

HRID 2205418Notes

Reaction equation

HRID 2205418 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:14](=O)[CH3:15])=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].B.C1COCC1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH2:14][CH3:15])=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuran2×HCID 13574130HCID 13574130, compound

Product 1

HCID 22627226HCID 22627226, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-acetyl-1H-indole-6-carboxylic acid methyl ester (0.65 g, 3.0 mmole) in THF (30 mL) was added BH3-THF (1.0M, 9 mL, 9 mmol). The solution was heated to reflux and then more BH3-THF (5 mL) was added. After allowing to cool and stirring for 2 hr at room temperature, the solvent was removed and the remaining material was diluted in ethyl acetate (100 mL) and washed with dilute NaHCO3 (200 mL). The organic layer was dried (MgSO4), filtered and concentrated. The remaining material was subjected to flash chromatography (25% ethyl acetate/hexanes) to collect 0.45 g (74% yield) of 3-ethyl-1H-indole-6-carboxylic acid methyl ester.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. temperatureto cool
  4. customthe solvent was removed
  5. additionthe remaining material was diluted in ethyl acetate (100 mL)
  6. washwashed with dilute NaHCO3 (200 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-736b00d711974b06b65f10cf98521320
Source dataset
uspto-grants-2016_06
Patent number
US09371281B2

Reaction notes

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