Triethylamine → HCID 68509481, compound

HRID 734984Notes

Reaction equation

HRID 734984 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.C(N([CH2:14][CH3:15])CC)C.[F:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[S:24](Cl)(=[O:26])=[O:25]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([N:8]([S:24]([C:15]2[CH:14]=[CH:18][C:17]([F:16])=[CH:22][C:21]=2[F:23])(=[O:26])=[O:25])[S:24]([C:18]2[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=2[F:16])(=[O:26])=[O:25])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 8176813-Amino-5-bromopyridineHCID 27342732,4-Difluorobenzenesulfonyl Chloride3×

Product 1

HCID 68509481HCID 68509481, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-bromo-3-pyridinamine (104 mmol) in dichloromethane (55 mL) was added dropwise over ˜60 min to a stirred solution of triethylamine (230 mmol) and 2,4-difluorobenzenesulfonyl chloride (235 mmol) in dichloromethane (300 mL). After 1.5 h, additional 2,4-difluorobenzenesulfonyl chloride (53.4 mmol) was added, and after 2 days, more 2,4-difluorobenzenesulfonyl chloride (47.0 mmol) and triethylamine (108 mmol) were added. After 1 h, the resulting mixture of mono- and bis-sulfonylation products was concentrated in vacuo and the residue was suspended in methanol (500 mL) and then filtered to provide N-(5-bromo-3-pyridinyl)-N-[(2,4-difluorophenyl)sulfonyl]-2,4-difluorobenzenesulfonamide as a white solid (54.4 mmol, 52%).

Workup

  1. waitafter 2 days
  2. waitAfter 1 h
  3. additionthe resulting mixture of mono- and bis-sulfonylation products
  4. concentrationwas concentrated in vacuo
  5. filtrationfiltered

Sources & evidence

ORD record
ord-ac1ce8fdc7c6410b90f76e65789f0c5b
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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