Sodium hydride → 2,2-dimethyl-propionic acid 5-bromo-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester

HRID 2234669Notes

Reaction equation

HRID 2234669 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:12]([CH2:16][CH3:17])[N:13]=[CH:14][CH:15]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[C:20]([O:26][CH2:27]Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:12]([CH2:16][CH3:17])[N:13]=[CH:14][CH:15]=3)=[CH:9][N:8]([CH2:27][O:26][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 1359620215-bromo-3-(2-ethyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 577314872,2-dimethyl-propionic acid 5-bromo-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-3-(2-ethyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridine was dissolved in N,N-dimethylforamide at 4° C. To the solution was added sodium hydride in small portions. The flask was warmed to room temperature and stirred for 1 hour. To the mixture was added chloromethyl pivalate. The reaction mixture was stirred for 2 hours at room temperature, and quenched with methanol. Saturated ammonium chloride solution was added, and the mixture was concentrated in vacuo. The residue was dissolved in dichloromethane, and the organic layer was washed four times with a saturated solution of sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in acetone. The insoluble residue remaining was filtered off and discarded. The filtrate was concentrated in vacuo and the crude material re-crystallized to afford 2,2-dimethyl-propionic acid 5-bromo-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester. MS: m/z 405.3+407.3 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred for 2 hours at room temperature
  2. customquenched with methanol
  3. additionSaturated ammonium chloride solution was added
  4. concentrationthe mixture was concentrated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washthe organic layer was washed four times with a saturated solution of sodium bicarbonate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. dissolutionThe residue was dissolved in acetone
  11. filtrationThe insoluble residue remaining was filtered off
  12. concentrationThe filtrate was concentrated in vacuo
  13. customthe crude material re-crystallized

Sources & evidence

ORD record
ord-b08ba0293e0740788ba6a2fe9491155a
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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