Picolinoyl Chloride Hydrochloride → N-(4-Chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)picolinamide

HRID 875737Notes

Reaction equation

HRID 875737 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].[Cl:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][N:15]=[C:14]2[NH:22][CH:23]=[C:24]([NH2:25])[C:13]=12>N1C=CC=CC=1>[Cl:11][C:12]1[C:17]([C:18]([F:21])([F:19])[F:20])=[CH:16][N:15]=[C:14]2[NH:22][CH:23]=[C:24]([NH:25][C:8](=[O:9])[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=3)[C:13]=12

Participants

4

Reactant 2

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

Product 1

HCID 60205407N-(4-Chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)picolinamideYield 80.6%

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-b]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-591264454cdd42bb93514ce3b8c1e817
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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