Acetonitrile → (3-Amino-2,6-difluorophenyl)(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)methanone

HRID 60083Notes

Reaction equation

HRID 60083 reaction equation
COC(=O)[NH:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([Br:23])[CH:21]=3)[NH:16][CH:15]=2)=[O:13])[C:6]=1[F:24].C(#N)C.C[Si](I)(C)C>C(OCC)(=O)C>[NH2:4][C:5]1[C:6]([F:24])=[C:7]([C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([Br:23])[CH:21]=3)[NH:16][CH:15]=2)=[O:13])[C:8]([F:11])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 85247Trimethylsilyl iodideHCID 58087834[3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-carbamic acid methyl ester

Product 1

HCID 58368727(3-Amino-2,6-difluorophenyl)(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)methanoneYield 103.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a reaction flask under nitrogen, [3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-carbamic acid methyl ester (6, 15.00 g, 36.6 mmol) is combined with 300 mL of anhydrous acetonitrile and trimethylsilyl iodide (21.95 g, 109.7 mmol). The reaction is stirred at room temperature overnight, then diluted with 500 mL of ethyl acetate and washed with 2×500 mL of 10% aqueous sodium thiosulfate. The aqueous layers are combined and back extracted with 1×500 mL of ethyl acetate. The organic layers are combined and washed with 1×500 mL of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound (7, 13.34 g).

Workup

  1. washwashed with 2×500 mL of 10% aqueous sodium thiosulfate
  2. extractionback extracted with 1×500 mL of ethyl acetate
  3. washwashed with 1×500 mL of saturated aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-7012cb630ff9420f9fa9448a57c4cf3d
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Reaction notes

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