4-Bromobenzoyl chloride → HCID 22709573, compound

HRID 352773Notes

Reaction equation

HRID 352773 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:6]([S:20]([N:23]1[CH2:28][C@H:27]([CH3:29])[NH:26][C@H:25]([CH3:30])[CH2:24]1)(=[O:22])=[O:21])=[CH:5]2.C(N(C(C)C)CC)(C)C.[Br:40][C:41]1[CH:49]=[CH:48][C:44]([C:45](Cl)=[O:46])=[CH:43][CH:42]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Br:40][C:41]1[CH:49]=[CH:48][C:44]([C:45]([N:26]2[CH:27]([CH3:29])[CH2:28][N:23]([S:20]([C:6]3[N:7]([S:11]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)(=[O:13])=[O:12])[C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=4)(=[O:21])=[O:22])[CH2:24][CH:25]2[CH3:30])=[O:46])=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 685154-Bromobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 69880793HCID 69880793, compound

Product 1

HCID 22709573HCID 22709573, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In dichloromethane (40 ml), cis-1-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]-3,5-dimethylpiperazine (1.30 g) was dissolved. To the resulting suspension, diisopropylethylamine (645 μl) was added under ice cooling, followed by the dropwise addition of a solution of 4-bromobenzoyl chloride (0.74 g) in dichloromethane (5 ml). Stirring was then effected at room temperature for 3 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction mixture. The organic layer thus separated was washed with 0.5N hydrochloric acid and saturated aqueous NaCl solution, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=2:1 to 1:1), whereby the title compound (1.8 g, 97%) was obtained as a pale yellow amorphous.

Workup

  1. customThe organic layer thus separated
  2. washwas washed with 0.5N hydrochloric acid and saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=2:1 to 1:1), whereby the title compound (1.8 g, 97%)
  7. customwas obtained as a pale yellow amorphous

Sources & evidence

ORD record
ord-d155e4580d474babb55837db827631c5
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…