Picolinoyl Chloride Hydrochloride → 2-Pyridinecarboxamide

HRID 1923777Notes

Reaction equation

HRID 1923777 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].ClC1C(C(F)(F)F)=C[N:15]=C2NC=C(N)C=12>N1C=CC=CC=1>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([NH2:15])=[O:9]

Participants

4

Reactant 2

HCID 135033Picolinoyl Chloride HydrochlorideHCID 602053084-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 150702-PyridinecarboxamideYield 224.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Picolinoyl chloride hydrochloride (270 mg, 1.53 mmol) was added to 4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-amine (240 mg, 1.02 mmol, Example 11, step G) in pyridine (5 mL). The reaction was stirred at 0° C. 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, and water (20 mL) was added. The solid formed was collected by filtration and dried to give N-(4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2, 3-1)]pyridin-3-yl)picolinamide (280 mg, 79% 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
  5. additionwater (20 mL) was added
  6. customThe solid formed
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-f7b928e91997432982ad5c72de8d48d6
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

Loading…