Pyridine → HCID 59026801, compound

HRID 658406Notes

Reaction equation

HRID 658406 reaction equation
N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[F:20][C:21]1[CH:26]=[C:25]([I:27])[CH:24]=[CH:23][C:22]=1[NH:28][C:29]1[CH:37]=[N:36][CH:35]=[C:34]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[F:44])[C:30]=1[C:31]([NH2:33])=O>O1CCOCC1>[F:20][C:21]1[CH:26]=[C:25]([I:27])[CH:24]=[CH:23][C:22]=1[NH:28][C:29]1[CH:37]=[N:36][CH:35]=[C:34]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[F:44])[C:30]=1[C:31]#[N:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 59026838HCID 59026838, compound

Product 1

HCID 59026801HCID 59026801, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Pyridine (28 μL, 0.35 mmol) and trifluoroacetic anhydride (27 μL, 0.19 mmol) were added to a solution of 3-(2-fluoro-4-iodo-phenylamino)-5-(2-fluoro-phenyl)-isonicotinamide (78 mg, 0.17 mmol) in dioxane (2 mL) at 0° C. The resulting solution was stirred for 3 h at room temperature. The reaction was quenched with 2M NaOH and stirred for 10 minutes. The reaction solution was diluted with EtOAc and satd. NH4Cl, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated to provide a precipitate. The precipitate was washed with MeOH and dried under vacuum to afford the desired product (60 mg, 80%). LC-MS (M+H=434, obsd.=434).

Workup

  1. customThe reaction was quenched with 2M NaOH
  2. stirringstirred for 10 minutes
  3. additionThe reaction solution was diluted with EtOAc and satd
  4. filtrationNH4Cl, and filtered through an Extrelut column
  5. washThe column was washed with EtOAc
  6. concentrationthe filtrate was concentrated
  7. customto provide a precipitate
  8. washThe precipitate was washed with MeOH
  9. customdried under vacuum

Sources & evidence

ORD record
ord-098622e23929431685869b0063c4686e
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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