Water → HCID 22997492, compound

HRID 1166188Notes

Reaction equation

HRID 1166188 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[O:18])[CH:12]=1.[OH-].[Na+].O>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:17]([C:13]1[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=1)[OH:18]

Participants

6

Reactant 4

HCID 962WaterHCID 103713-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 678615-Fluoroindole

Product 1

HCID 22997492HCID 22997492, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 5-fluoroindole (4 g, 30 mmol) in methanol is treated with 3-pyridine carboxaldehyde (2.79 ml, 30 mmol), cooled to 0° C., treated with 50% NaOH (3.25 ml), stirred at 0° C. for 1 hr, warmed to room temperature, stirred for 3 hr, treated with water and extracted with ethyl acetate. The extracts are combined, dried over Na2SO4 and concentrated in vacuo. The residue is treated with ethyl acetate and filtered. The filtrate is further concentrated and filtered. The filtercakes are combined and dried to afford the title compound as a pale orange solid 5.2 g (73%) mp 131-133° C., identified by NMR and mass spectral analyses.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 3 hr
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. additionThe residue is treated with ethyl acetate
  7. filtrationfiltered
  8. concentrationThe filtrate is further concentrated
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-4d2c2c917c5e46b1a9f120febd5d96e7
Source dataset
uspto-grants-2003_09
Patent number
US06613781B2

Reaction notes

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