N-Iodosuccinimide → HCID 58886665, compound

HRID 494716Notes

Reaction equation

HRID 494716 reaction equation
[I:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]([C:13]1[C:14]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=2[F:31])=[C:15]([F:22])[C:16]2[N:17]([CH:19]=[CH:20][N:21]=2)[CH:18]=1)=[O:12]>C(#N)C.C(OCC)(=O)C>[CH3:9][O:10][C:11]([C:13]1[C:14]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=2[F:31])=[C:15]([F:22])[C:16]2[N:17]([C:19]([I:1])=[CH:20][N:21]=2)[CH:18]=1)=[O:12]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 58886662HCID 58886662, compound

Product 1

HCID 58886665HCID 58886665, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-iodosuccinimide (134 mg, 0.60 mmol) was added in a single portion to a solution of 8-fluoro-7-(2-fluoro-4-methylphenylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (172 mg, 0.54 mmol) in acetonitrile (10 mL) resulting in a thick precipitate after ten minutes of stirring. The suspension was diluted with ethyl acetate, washed with NaHSO3, saturated NaHCO3, water, brine, and dried over Na2SO4. Concentration provided the desired product as a yellow solid (241 mg, 100%). MS APCI (+) m/z 444 (M+1) detected. 1H NMR (400 MHz, CD3OD) δ 8.78 (s, 1H), 7.62 (s, 1H), 6.95 (m, 3H), 4.00 (s, 3H), 2.33 (s, 3H). 19F NMR (376 MHz, CD3OD)−131.11 (s, 1F), −146.71 (s, 1F).

Workup

  1. customresulting in a thick precipitate after ten minutes
  2. washwashed with NaHSO3, saturated NaHCO3, water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationConcentration

Sources & evidence

ORD record
ord-3aefaad045ef4bf3bc87f600075c9f09
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

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