Pyridine → N-{2,4-difluoro-3-[5-(2-methyl-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-2-fluoro-benzenesulfonamide

HRID 60117

Reaction equation

HRID 60117 reaction equation
[NH2:1][C:2]1[C:3]([F:27])=[C:4]([C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[N:22][C:23]([CH3:26])=[N:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)=[O:10])[C:5]([F:8])=[CH:6][CH:7]=1.[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[S:35](Cl)(=[O:37])=[O:36].N1C=CC=CC=1>O1CCCC1>[F:27][C:3]1[C:4]([C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[N:22][C:23]([CH3:26])=[N:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)=[O:10])=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[NH:1][S:35]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[F:28])(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1377612-Fluorobenzenesulphonyl chlorideHCID 58368924(3-amino-2,6-difluoro-phenyl)-[5-(2-methyl-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methanone

Product 1

HCID 58368889N-{2,4-difluoro-3-[5-(2-methyl-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-2-fluoro-benzenesulfonamideYield 41.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To (3-amino-2,6-difluoro-phenyl)-[5-(2-methyl-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methanone (50, 0.220 g, 0.602 mmol) in 4.01 mL of tetrahydrofuran, 2-fluoro-benzenesulfonyl chloride (20, 0.352 g, 1.807 mmol) and pyridine (0.146 mL, 1.807 mmol) are added and the reaction is heated at 60° C. overnight. The reaction is partitioned between brine/water and ethyl acetate/tetrahydrofuran. The organic layer is separated and the solvent is removed under vacuum. The resulting residue is purified by silica gel column chromatography eluting with 0-10% methanol in dichloromethane, then triturated with ethyl acetate/heptane to provide the desired compound as a light tan solid (P-1520, 0.130 g, 0.248 mmol, 41.2% yield).

Workup

  1. customThe reaction is partitioned between brine/water and ethyl acetate/tetrahydrofuran
  2. customThe organic layer is separated
  3. customthe solvent is removed under vacuum
  4. customThe resulting residue is purified by silica gel column chromatography
  5. washeluting with 0-10% methanol in dichloromethane
  6. customtriturated with ethyl acetate/heptane

Sources & evidence

ORD record
ord-53d00a5c543c4c6fb3ebbf5ed8078eea
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Linked notes

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