Cyclopropanecarbonyl chloride → N-(5-ethoxy-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopropanecarboxamide

HRID 2203963Notes

Reaction equation

HRID 2203963 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[CH2:7]([O:9][C:10]1[C:11]([F:20])=[C:12]2[C:18]([NH2:19])=[CH:17][NH:16][C:13]2=[N:14][CH:15]=1)[CH3:8]>N1C=CC=CC=1>[CH2:7]([O:9][C:10]1[C:11]([F:20])=[C:12]2[C:18]([NH:19][C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])=[CH:17][NH:16][C:13]2=[N:14][CH:15]=1)[CH3:8]

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 602056395-ethoxy-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205640N-(5-ethoxy-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopropanecarboxamideYield 55.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cyclopropanecarbonyl chloride (63.1 μL, 0.676 mmol) was added dropwise to 5-ethoxy-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (120 mg, 0.615 mmol) in pyridine (5 mL) at 0° C. The reaction was stirred at about 0 to about 5° C. for 2 hours and then concentrated to dryness. Water (10 mL) was added and extracted with CHCl3/IPA (3:1). The combined organic phases were dried over MgSO4 and concentrated to yield N-(5-ethoxy-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopropanecarboxamide (90 mg, 55% yield) as a solid.

Workup

  1. concentrationconcentrated to dryness
  2. additionWater (10 mL) was added
  3. extractionextracted with CHCl3/IPA (3:1)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3b5312c08a424c39bcbb713583fbd5d7
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

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