4-Pyridinecarboxaldehyde → (5-fluoro-1H-indol-3-yl)-pyridin-4-yl-methanol

HRID 1166184Notes

Reaction equation

HRID 1166184 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][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=1.[OH-].[Na+]>CO.O>[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:14]1[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=1)[OH:18]

Participants

6

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 678615-Fluoroindole

Product 1

HCID 11322446(5-fluoro-1H-indol-3-yl)-pyridin-4-yl-methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 5-fluoroindole (3.10 g, 23.0 mmol) in methanol is treated with 4-pyridinecarbox-aldehyde (2.20 ml, 23.0 mmol), then treated with aqueous NaOH (2.5 ml, 50%) at 0° C., stirred for 1 hr at 0° C., warmed to room temperature, stirred for 3 hr. and diluted with water. The resultant mixture is filtered. The filtercake is dried under vacuum to afford the title product as a light yellow solid, 5.2 g (93%) mp 171-173° C., identified by mass spectral and NMR analyses.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 3 hr
  3. filtrationThe resultant mixture is filtered
  4. customThe filtercake is dried under vacuum

Sources & evidence

ORD record
ord-13133ef2ac8146f0bf2b894b8a99c993
Source dataset
uspto-grants-2003_09
Patent number
US06613781B2

Reaction notes

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