Sodium Bicarbonate → HCID 39733625, compound

HRID 239201Notes

Reaction equation

HRID 239201 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)[CH3:2].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][NH:11]2)[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 16090868HCID 16090868, compound

Product 1

HCID 39733625HCID 39733625, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of commercially available 4-hydroindole (compound 1, 0.226 g, 1.7 mmol) and potassium carbonate (0.704 g, 5.1 mmol) in acetone was added ethyl bromoacetate (0.3 mL, 2.6 mmol). The reaction mixture was stirred at RT for 18 h, and then filtered. The solvent was removed and the green oil was purified by flash chromatography [hexanes-ethyl acetate (4:1)] to give ethyl(indol-4-yloxy)acetate. NMR: δ (300 MHz, CDCl3) 8.2 (br s, 1H), 7.13 (dd, J=5.6, 2.3 Hz, 1H), 7.1-7.06 (m, 2H), 6.73 (t, J=2.4 Hz), 6.43 (dd, J=5.9, 2.7 Hz, 1H), 4.78 (s, 2H), 4.28 (q, J=7.4 Hz, 2H), 1.31 (t, J=7.4 Hz, 3H). To a solution of this indole in acetic acid (10 mL) was added sodium cyanoborohydride (0.302 g, 4.8 mmol) as a solid. The reaction mixture was stirred at RT for 18 h, then neutralized with aqueous sodium bicarbonate and extracted with diethyl ether. The solvent was removed to give compound 2a (0.308 g, 88% yield) as a colorless oil. NMR: δ (300 MHz, CDCl3) 6.98 (d, J=7.9 Hz, 1H), 6.39 (t, J=7.9 Hz, 1H), 6.18 (d, J=7.9 Hz, 1H), 4.62 (s, 2H), 4.28 (q, J=7.0, Hz, 2H), 3.58 (t, J=8.4 Hz, 2H), 3.07 (t, J=8.4 Hz, 2H), 1.30 (t, J=7.0 Hz, 3H).

Workup

  1. extractionextracted with diethyl ether
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-3c176895f20b4d6bb597e2e2fa1a9287
Source dataset
uspto-grants-2014_02
Patent number
US08642785B2

Reaction notes

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