N-Iodosuccinimide → HCID 59026830, compound

HRID 658401Notes

Reaction equation

HRID 658401 reaction equation
[I:1]N1C(=O)CCC1=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:21][O:22][C:23](=[O:45])[C:24]1[C:29]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])=[CH:28][N:27]=[CH:26][C:25]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[F:44]>>[CH3:21][O:22][C:23](=[O:45])[C:24]1[C:29]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([I:1])=[CH:33][C:32]=2[F:37])=[CH:28][N:27]=[CH:26][C:25]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[F:44]

Participants

4

Reactant 3

HCID 120273N-IodosuccinimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 59026768HCID 59026768, compound

Product 1

HCID 59026830HCID 59026830, compoundYield 78.5%

Conditions

Temperature
60 °C

Procedure

N-iodosuccinimide (400 mg, 1.76 mmol) and p-toluenesulfonic acid monohydrate (670 mg, 3.53 mmol) were added to a solution of 3-(2-fluoro-phenyl)-5-(2-fluoro-phenylamino)-isonicotinic acid methyl ester (480 mg, 1.41 mmol), and stirred overnight at 60° C. The reaction mixture was quenched with Na2S2O3 (1 mL, 10% aqueous solution), diluted with CH2Cl2, and filtered through an Extrelut column. The column was washed with CH2Cl2, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 0 to 55% EtOAc in hexanes to afford the desired product (516 mg, 78%). LC-MS (M+H=467, obsd.=467).

Workup

  1. customThe reaction mixture was quenched with Na2S2O3 (1 mL, 10% aqueous solution)
  2. additiondiluted with CH2Cl2
  3. filtrationfiltered through an Extrelut column
  4. washThe column was washed with CH2Cl2
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified via Biotage
  7. washeluting with a gradient of 0 to 55% EtOAc in hexanes

Sources & evidence

ORD record
ord-a3cbd894efe34110bacfd64b1a555974
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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