Sodium Bicarbonate → 4-Chloro-2-(5-chloro-2-fluoro-phenyl)-[1,8]naphthyridine

HRID 1629910Notes

Reaction equation

Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([F:23])=[C:18](B(O)O)[CH:19]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:12][C:10]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([C:16]2[CH:15]=[C:14]([Cl:13])[CH:19]=[CH:18][C:17]=2[F:23])[CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 9.95 g (50.0 mmol) 2,4-dichloro-[1,8]naphthyridine, 8.72 g (50.0 mmol) 5-chloro-2-fluorophenylboronic acid and 5.04 g (60.0 mmol) sodium bicarbonate in 100 ml DMF and 50 ml water was heated to 80° C. under nitrogen. 701 mg (1.0 mmol) bis-(triphenylphosphine)-palladium(II)-chloride were added and the mixture was stirred for 16 hrs at 80° C. Water was added to the reaction mixture and the precipitate was filtered off, dried in vacuum and recrystallized from 2-propanol: 4-chloro-2-(5-chloro-2-fluoro-phenyl)-[1,8]naphthyridine as slightly yellow crystals; HPLC-MS: 2.49 min, [M+H] 293.

Workup

filtrationthe precipitate was filtered off
customdried in vacuum
customrecrystallized from 2-propanol
custom2.49 min, [M+H] 293

Sources & evidence

ORD record: ord-89933d479177431a8db8d9db202e9b3f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791113B2

Reaction notes

Loading…