5-Fluorogramine → 5-fluoro-3-(2-pyridin-3-yl-vinyl)-1H-indole

HRID 2382045Notes

Reaction equation

HRID 2382045 reaction equation
CN([CH2:4][C:5]1[C:9]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]=2[NH:7][CH:6]=1)C.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=O)[CH:16]=1.P(CCCC)(CCCC)CCCC>CC#N>[F:14][C:11]1[CH:10]=[C:9]2[C:8](=[CH:13][CH:12]=1)[NH:7][CH:6]=[C:5]2[CH:4]=[CH:21][C:17]1[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 95765-FluorogramineHCID 103713-PyridinecarboxaldehydeHCID 13831Tributylphosphine

Product 1

HCID 685566735-fluoro-3-(2-pyridin-3-yl-vinyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 5-fluorogramine (576 mg, 3 mmol) and pyridine-3-carboxaldehyde (531 mg, 3 mmol) in MeCN (6 mL) is treated with Bu3P (1.12 mL, 4.5 mmol) and stirred at 90° C. for 24 h. The mixture is concentrated, filtered through a pad of silica gel eluting with 30% EtOAc in heptane to afford 5-fluoro-3-(2-pyridin-3-yl-vinyl)-1H-indole as a mixture of olefin isomers, which is used in the next step without further purification.

Workup

  1. concentrationThe mixture is concentrated
  2. filtrationfiltered through a pad of silica gel eluting with 30% EtOAc in heptane

Sources & evidence

ORD record
ord-5eec87a0265840689371f9cedbba3d80
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

Loading…