N-Iodosuccinimide → HCID 59026841, compound

HRID 658396Notes

Reaction equation

HRID 658396 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[Cl: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[Cl:44]

Participants

4

Reactant 3

HCID 120273N-IodosuccinimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 59026840HCID 59026840, compound

Product 1

HCID 59026841HCID 59026841, compoundYield 85%

Conditions

Temperature
60 °C

Procedure

N-iodosuccinimide (236 mg, 1.05 mmol) and p-toluenesulfonic acid monohydrate (400 mg, 2.1 mmol) were added to a solution of 3-(2-chloro-phenyl)-5-(2-fluoro-phenylamino)-isonicotinic acid methyl ester (300 mg, 0.84 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 (343 mg, 85%). LC-MS (M+H=483, obsd.=483).

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-b86397f12d9a4ae4a0dbc32390a9a089
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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