Pivaloyl chloride → HCID 67045240, compound

HRID 408209Notes

Reaction equation

HRID 408209 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Br:8][C:9]1[C:10]([F:19])=[C:11]2[C:17]([NH2:18])=[CH:16][NH:15][C:12]2=[N:13][CH:14]=1>N1C=CC=CC=1>[Br:8][C:9]1[C:10]([F:19])=[C:11]2[C:17]([NH:18][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[CH:16][NH:15][C:12]2=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 67045240HCID 67045240, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Pivaloyl chloride (0.12 mL, 0.98 mmol) was added to 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (0.15 g, 0.65 mmol) in pyridine (5 mL). The reaction was stirred at room temperature for 10 minutes, and then the pyridine was removed. THF (5 mL) and 2N LiOH (3 mL) were added and stirred for 20 minutes. The THF was removed in vacuo, and water (20 mL) was added to the aqueous residue. The solid formed was collected by filtration and dried to give N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pivalamide (0.128 g, 62% yield) as a solid.

Workup

  1. customthe pyridine was removed
  2. additionTHF (5 mL) and 2N LiOH (3 mL) were added
  3. stirringstirred for 20 minutes
  4. customThe THF was removed in vacuo, and water (20 mL)
  5. additionwas added to the aqueous residue
  6. customThe solid formed
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-9851befb012d438ba3e6a7103911fb54
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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