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

HRID 2376627
Notes
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Reaction equation

HRID 2376627 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 107055713-(6-Amino-1,7-naphthyridin-8-yl)benzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 178962836-Trifluromethanesulfonyl-8-(3 cyanophenyl)-1,7-naphthyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. customThe cooling bath is then removed
  2. stirringthe mixture stirred at room temperature for 3 hours
  3. additionThe resulting mixture is diluted with ethyl acetate
  4. washwashed with water, 2M NaOH and water again
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes