Chlorosulfonic acid → 5-fluoro-1-{[2-(3-fluorophenyl)pyrimidine-5-carbonyl]amino}-1H-indole-3-sulfonyl chloride

HRID 2381934Notes

Reaction equation

HRID 2381934 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([NH:11][C:12]([C:14]1[CH:15]=[N:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[N:18][CH:19]=1)=[O:13])[CH:6]=[CH:5]2.[Cl:27][S:28](O)(=[O:30])=[O:29]>CC#N>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([NH:11][C:12]([C:14]1[CH:15]=[N:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[N:18][CH:19]=1)=[O:13])[CH:6]=[C:5]2[S:28]([Cl:27])(=[O:30])=[O:29]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 25099830HCID 25099830, compound

Product 1

HCID 866393645-fluoro-1-{[2-(3-fluorophenyl)pyrimidine-5-carbonyl]amino}-1H-indole-3-sulfonyl chlorideYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(3-fluorophenyl)pyrimidine-5-carboxylic acid-(5-fluoroindol-1-yl)amide (0.35 g,) in dry CH3CN (20 mL) is treated with chlorosulfonic acid (0.5 mL) and stirred at rt for 24 h. The reaction mixture is poured onto ice/water (150 mL) and extracted with EtOAc. The organic layer is washed with water, brine and dried (MgSO4), filtered and concentrated in vacuo to afford 5-fluoro-1-{[2-(3-fluorophenyl)pyrimidine-5-carbonyl]amino}-1H-indole-3-sulfonyl chloride (0.43 g, 95%). MS: 449 (M+H).

Workup

  1. additionThe reaction mixture is poured onto ice/water (150 mL)
  2. extractionextracted with EtOAc
  3. washThe organic layer is washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a86ab4439d94f558f6036a0c84390d6
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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