N-Iodosuccinimide → 1-benzyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-3-iodo-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 574996Notes

Reaction equation

HRID 574996 reaction equation
C(=O)([O-])O.[Na+].[I:6]N1C(=O)CCC1=O.[CH2:14]([N:21]1[C:25]2[N:26]=[C:27]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[C:35]([C:40]([O:42][CH3:43])=[O:41])[CH:34]=3)[CH:28]=[C:29]([C:30]([OH:32])=[O:31])[C:24]=2[CH:23]=[N:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCOCC1>[CH2:14]([N:21]1[C:25]2[N:26]=[C:27]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[C:35]([C:40]([O:42][CH3:43])=[O:41])[CH:34]=3)[CH:28]=[C:29]([C:30]([OH:32])=[O:31])[C:24]=2[C:23]([I:6])=[N:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 516892Sodium Bicarbonate2×HCID 1177778991-benzyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 1177779471-benzyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-3-iodo-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium hydrogen carbonate (11.39 g/0.136 mol) and N-iodosuccinimide (30.51 g/0.136 mol) are added portionwise to a suspension of 1-benzyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (14.25 g/45.2 mmol) in 410 mL of dioxane. The reaction mixture is stirred for 24 h at ambient temperature. The reaction medium is run into a saturated aqueous solution of NaHCO3. The aqueous phase is washed with EtOAc and then acidified to pH=2-3 using a solution of KHSO4 (1 M), and extracted with EtOAc. The organic phase is washed with water, with a solution of sodium thiosulphate (0.1 M) and with a saturated aqueous solution of NaCl, dried over sodium sulphate and then concentrated to dryness to give 13.9 g of a yellow powder (yield: 70%).

Workup

  1. washThe aqueous phase is washed with EtOAc
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with water, with a solution of sodium thiosulphate (0.1 M) and with a saturated aqueous solution of NaCl
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-28997d62afa446dcb21ba09be14ec485
Source dataset
uspto-grants-2015_05
Patent number
US09034898B2

Reaction notes

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