2-Fluoropyridine → methyl 1-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 529046Notes

Reaction equation

[H-].[Na+].[NH:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]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:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4]1

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium hydride (22.70 mg, 0.568 mmol, 60% suspension in mineral oil) was added to a solution of methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate (100 mg, 0.568 mmol) in DMF (1419 μl) at RT. After 10 min, 2-fluoropyridine (48.8 μl, 0.568 mmol) was added to the mixture and the mixture was heated at 100° C. for 14 h. After being cooled to RT, the reaction mixture was directly purified by HPLC followed by neutralization (aq. NaHCO3) to afford the title compound as a colorless film.

Workup

temperatureAfter being cooled to RT
customthe reaction mixture was directly purified by HPLC

Sources & evidence

ORD record: ord-01b08f1cd13447608ead7ecedc27a135
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346829B2

Reaction notes

Loading…