Acetic Acid → 2-[(5-Fluoro-1H-indol-7-ylmethyl)-amino]-ethanol

HRID 2167050Notes

Reaction equation

HRID 2167050 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].C(O)(=O)C.[F:9][C:10]1[CH:11]=[C:12]2[C:16](=[C:17]([CH:19]=O)[CH:18]=1)[NH:15][CH:14]=[CH:13]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+].[OH-].[Na+]>ClCCCl>[F:9][C:10]1[CH:11]=[C:12]2[C:16](=[C:17]([CH2:19][NH:1][CH2:2][CH2:3][OH:4])[CH:18]=1)[NH:15][CH:14]=[CH:13]2

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 700EthanolamineHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 179856705-fluoro-1H-indole-7-carbaldehyde

Product 1

HCID 118165992-[(5-Fluoro-1H-indol-7-ylmethyl)-amino]-ethanolYield 96%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Add 2-aminoethanol (1.93 mL, 32.0 mmol) followed by acetic acid (2.01 mL, 48.0 mmol) to a solution of 5-fluoro-1H-indole-7-carbaldehyde (2.6 g, 16.0 mmol) in 1,2-dichloroethane (40 mL). Stir at room temperature for 15 minutes. Add sodium triacetoxyborohydride (4.07 g, 19.2 mmol) portion wise. Stir the reaction mixture at room temperature for 3 hours. Add saturated aqueous sodium bicarbonate (100 mL) slowly followed by 1 N NaOH to pH ˜9. Extract with ethyl acetate (100 mL×3). Wash the organic phase with saturated aqueous sodium chloride (200 mL×2), dry over sodium sulfate, and concentrate under reduced pressure to provide the desired compound as a pale yellow solid (3.2 g, 96%).

Workup

  1. stirringStir the reaction mixture at room temperature for 3 hours
  2. extractionExtract with ethyl acetate (100 mL×3)
  3. washWash the organic phase with saturated aqueous sodium chloride (200 mL×2)
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-cffe7212934b47de8f1c407526e4f5a9
Source dataset
uspto-grants-2015_06
Patent number
US09044487B2

Reaction notes

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