Methyl iodide → HCID 57516853, compound

HRID 451211Notes

Reaction equation

HRID 451211 reaction equation
C(O[C:6](=O)[NH:7][C:8]1[C:9]([Cl:19])=[C:10]2[CH:16]=[N:15][N:14]([CH2:17][CH3:18])[C:11]2=[N:12][CH:13]=1)(C)(C)C.[H-].[Na+].IC>CN(C=O)C>[Cl:19][C:9]1[C:8]([NH:7][CH3:6])=[CH:13][N:12]=[C:11]2[N:14]([CH2:17][CH3:18])[N:15]=[CH:16][C:10]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67441160HCID 67441160, compound

Product 1

HCID 57516853HCID 57516853, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-carbamic acid tert-butyl ester (3.3 g, 11.1 mmol) in DMF (50 mL) at 0° C. was added NaH (0.694 g, 50% purity, 14.5 mmol). After 20 minutes, iodomethane (2.37 g, 16.7 mmol) was added and the temperature raised to RT. The reaction was quenched by addition of H2O and the product extracted with EtOAc. The combined organic phases were dried over Na2SO4, and concentrated under vacuo to give a crude intermediate which was used directly in the next step without further purification. This residue as dissolved in CH2Cl2 (50 mL) and TFA (10 mL) was added. The reaction mixture was heated at 30° C. for 3 hours, diluted with CH2Cl2 (100 mL) and aqueous NaOH (1N) was added until pH reached 8. The organic phase was dried over Na2SO4, concentrated under vacuo to give the title product 2.24 g with high purity (no further purification needed) (96%) as a light yellow solid. ES-MS m/e: 211.2 (M+H+).

Workup

  1. customThe reaction was quenched by addition of H2O
  2. extractionthe product extracted with EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated under vacuo
  5. customto give a crude intermediate which
  6. customwas used directly in the next step without further purification
  7. dissolutionThis residue as dissolved in CH2Cl2 (50 mL)
  8. additionTFA (10 mL) was added
  9. temperatureThe reaction mixture was heated at 30° C. for 3 hours
  10. additiondiluted with CH2Cl2 (100 mL) and aqueous NaOH (1N)
  11. additionwas added until pH
  12. dry with materialThe organic phase was dried over Na2SO4
  13. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-d122d469fae1459d8b7bc4e8a3eb3dad
Source dataset
uspto-grants-2013_07
Patent number
US08487102B2

Reaction notes

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