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

HRID 2376627Notes

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 dimethyl-formamide (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, 2M 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.

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, 2M 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-83f32037ac3943768f0eca4b17857ce6
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468370B2

Reaction notes

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