Acetonitrile → HCID 66647207, compound

HRID 1397854Notes

Reaction equation

HRID 1397854 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[C:26]([C:29]#[N:30])[CH:27]=3)[NH:22][CH:21]=2)=[O:19])[C:12]=1[F:31])C1C=CC=CC=1.C(#N)C.C[Si](I)(C)C>CO>[NH2:10][C:11]1[C:12]([F:31])=[C:13]([C:14]([F:17])=[CH:15][CH:16]=1)[C:18]([C:20]1[C:28]2[C:23](=[N:24][CH:25]=[C:26]([C:29]#[N:30])[CH:27]=2)[NH:22][CH:21]=1)=[O:19]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 85247Trimethylsilyl iodideHCID 67134953HCID 67134953, compound

Product 1

HCID 66647207HCID 66647207, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a reaction vessel, [3-(5-cyano-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-carbamic acid benzyl ester (27, 1.78 g, 4.12 mmol), 36 mL of anhydrous acetonitrile and trimethylsilyl iodide (3.29 g, 16.47 mmol) were added under nitrogen and the reaction was stirred at room temperature overnight. The reaction mixture was diluted with 20 mL of methanol and the solvents removed under vacuum. The residue was diluted with 50 mL of 2 M sodium hydroxide, and extracted with 3×50 mL of ethyl acetate. The organic layers were combined and washed with 200 mL of 10% sodium thiosulfate, then 200 mL of brine, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The crude material was slurried in methanol, the solids collected by filtration and dried to give the desired compound (28, 0.74 g, 60%).

Workup

  1. customthe solvents removed under vacuum
  2. additionThe residue was diluted with 50 mL of 2 M sodium hydroxide
  3. extractionextracted with 3×50 mL of ethyl acetate
  4. washwashed with 200 mL of 10% sodium thiosulfate
  5. dry with material200 mL of brine, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. filtrationthe solids collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-640c927a969b4977be8e80cbb3ae9a84
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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