Trifluoromethanesulfonic acid → 6-Trifluromethanesulfonyl-8-(3 cyanophenyl)-1,7-naphthyridine

HRID 917307Notes

Reaction equation

N[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=3)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[F:20][C:21]([F:27])([F:26])[S:22](O)(=[O:24])=[O:23].N([O-])=O.[Na+]>CN(C)C=O>[F:20][C:21]([F:27])([F:26])[S:22]([C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=3)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)(=[O:24])=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-amino-8-(3-cyanophenyl)-1,7-naphthyridine (4.058 g) in dimethylform-amide (DMF) (22 ml) under argon at 0° C. is added trifluoromethanesulfonic acid (11 ml). The mixture is stirred at 0° C. for 10 minutes and then sodium nitrite (2.26 g) is added slowly. The cooling bath is then removed and the mixture stirred at room temperature for 3 hours. The resulting mixture is diluted with ethyl acetate and washed with water, 2 M NaOH and water again. The organic layer is dried over sodium sulfate, then concentrated in vacuo and purified by column chromatography, eluting with 10:0.5 toluene:acetone to yield the title compound. M.p. 102-104° C. MS (m/e)=380.1

Workup

customThe cooling bath is then removed
stirringthe mixture stirred at room temperature for 3 hours
additionThe resulting mixture is diluted with ethyl acetate
washwashed with water, 2 M NaOH and water again
dry with materialThe organic layer is dried over sodium sulfate
concentrationconcentrated in vacuo
custompurified by column chromatography
washeluting with 10:0.5 toluene

Sources & evidence

ORD record: ord-211fb7ef9b5440afb209a0f98817808e
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273875B2

Reaction notes

Loading…