2-Fluoropyridine → HCID 86708888, compound

HRID 1471429Notes

Reaction equation

HRID 1471429 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4]1.F[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>CN(C=O)C>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4]1

Participants

5

Reactant 3

HCID 97462-FluoropyridineHCID 24758Sodium hydrideHCID 589098Methyl indole-3-carboxylate

Product 1

HCID 86708888HCID 86708888, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

Sodium hydride (45.7 mg, 1.142 mmol, 60% dispersion in mineral oil) was added to a solution of methyl 1H-indole-3-carboxylate (200 mg, 1.142 mmol) in DMF (2283 μl) at RT. After 30 min, 2-fluoropyridine (99 μl, 1.142 mmol) was added to the mixture and the resulting suspension was heated at 120° C. for 14 h. The reaction mixture was diluted with DMF, filtered, and purified by HPLC to afford the title compound as a white solid.

Workup

  1. filtrationfiltered
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-24218949af634c6bbc42b4b40c8b6ff7
Source dataset
uspto-grants-2015_04
Patent number
US09012447B2

Reaction notes

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