Sodium Hydroxide → 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide

HRID 456662Notes

Reaction equation

HRID 456662 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[NH:12][CH:13]=[CH:14][CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:16][C:17]1[N:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20].[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[NH:12][C:13]([C:19]([C:18]3[C:17]([Cl:16])=[N:25][CH:24]=[CH:23][CH:22]=3)=[O:20])=[CH:14][CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 27745412-Chloronicotinoyl chlorideHCID 51210759HCID 51210759, compound

Product 1

HCID 865922445-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amideYield 18.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide (1.56 g, 7.6 mmol) and 2-chloronicotinoyl chloride (1.925 g, 10.9 mmol) in benzene (15 mL) at 0° C. was added dropwise a solution of tin (IV) chloride (3.5 g) in dry benzene (5 mL). The mixture was allowed to warm up slowly to room temperature and stirred for 4 hours. The reaction was added with NaOH (100 mL) and extracted with ethyl acetate, washed with brine (2×), dried and concentrated. The residue was purified on a silica gel column to give 477 mg (18%) of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine (2×)
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-719fc771f4b743e2bf7eba4e8f0432d8
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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