Triphenylphosphine → 6-Chloro-5-fluoro-2-(quinolin-6-ylamino)nicotinonitrile

HRID 340440Notes

Reaction equation

HRID 340440 reaction equation
[Cl:1]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:28][C:29]1[C:34](=O)[NH:33][C:32]([NH:36][C:37]2[CH:38]=[C:39]3[C:44](=[CH:45][CH:46]=2)[N:43]=[CH:42][CH:41]=[CH:40]3)=[C:31]([C:47]#[N:48])[CH:30]=1>O1CCOCC1>[Cl:1][C:34]1[C:29]([F:28])=[CH:30][C:31]([C:47]#[N:48])=[C:32]([NH:36][C:37]2[CH:38]=[C:39]3[C:44](=[CH:45][CH:46]=2)[N:43]=[CH:42][CH:41]=[CH:40]3)[N:33]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 686063515-Fluoro-6-oxo-2-(quinolin-6-ylamino)-1,6-dihydropyridin-3-carbonitrile

Product 1

HCID 866838496-Chloro-5-fluoro-2-(quinolin-6-ylamino)nicotinonitrileYield 84.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A 1,4-dioxane (100 ml) solution containing N-chlorosuccinimide (4.15 g) was added dropwise to a 1,4-dioxane (50 ml) solution containing triphenylphosphine (8.58 g) at 50° C., followed by stirring for 30 minutes. 5-fluoro-6-oxo-2-(quinolin-6-ylamino)-1,6-dihydropyridin-3-carbonitrile (2.61 g) was added to the reaction mixture, followed by stirring at 70° C. for 3 hours. The reaction mixture was cooled to room temperature. Then solid matter was collected by filtration and was washed with tetrahydrofuran, and a gray solid of 6-chloro-5-fluoro-2-(quinolin-6-ylamino)nicotinonitrile (2.34 g) was thus obtained.

Workup

  1. stirringby stirring at 70° C. for 3 hours
  2. filtrationThen solid matter was collected by filtration
  3. washwas washed with tetrahydrofuran

Sources & evidence

ORD record
ord-cd0ba520cade43dd9705bd958faa96f6
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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