3-Pyridinecarbonyl chloride, hydrochloride (1:1) → HCID 60205314, compound

HRID 2203752Notes

Reaction equation

HRID 2203752 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[F:11][C:12]1[C:17]([F:18])=[CH:16][N:15]=[C:14]2[NH:19][CH:20]=[C:21]([NH2:22])[C:13]=12>N1C=CC=CC=1>[F:11][C:12]1[C:17]([F:18])=[CH:16][N:15]=[C:14]2[NH:19][CH:20]=[C:21]([NH:22][C:2](=[O:9])[C:3]3[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=3)[C:13]=12

Participants

4

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 60205313HCID 60205313, compound

Product 1

HCID 60205314HCID 60205314, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Nicotinoyl chloride hydrochloride (0.70 g, 3.90 mmol) was added to 4,5-difluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (0.22 g, 1.30 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 the reaction was stirred for 20 minutes. The THF was removed, and water (20 mL) was added. The solid formed was collected by filtration and dried to give N-(4,5-difluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.33 g, 92% yield) as a solid.

Workup

  1. customthe pyridine was removed
  2. additionTHF (5 mL) and 2N LiOH (3 mL) were added
  3. stirringthe reaction was stirred for 20 minutes
  4. customThe THF was removed
  5. additionwater (20 mL) was added
  6. customThe solid formed
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-3c185f9505ef417c810960272b232872
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

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