5-Carboxy-3-(2,4-dichlorobenzyl)indole → 3-(2,4-Dichlorobenzyl)-5-(1-pentanesulfonylcarbamoyl)indole

HRID 2187755Notes

Reaction equation

HRID 2187755 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])([OH:3])=O.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.[CH2:44]([S:49]([NH2:52])(=[O:51])=[O:50])[CH2:45][CH2:46][CH2:47][CH3:48]>O>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[CH2:13][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([C:1](=[O:3])[NH:52][S:49]([CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])(=[O:51])=[O:50])[CH:5]=2)[NH:9][CH:8]=1

Participants

5

Reactant 3

HCID 98800965-Carboxy-3-(2,4-dichlorobenzyl)indoleHCID 109206961-PentanesulfonamideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 219382503-(2,4-Dichlorobenzyl)-5-(1-pentanesulfonylcarbamoyl)indoleYield 42.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N,N′-Carbonyldiimidazole (0.282 g) is added to an N,N-dimethylfornamide (4.3 ml) solution of 5-carboxy-3-(2,4-dichlorobenzyl)indole (0.429 g), and stirred at room temperature for 1 hour. Diazabicycloundecene (0.306 g) and 1-pentanesulfonamide (0.304 g) are added thereto, and stirred at 100° C. for 40 hours. The reaction mixture is cooled, and then made acidic with water and 1M HCI added thereto. Then, the gummy residue formed is collected. This is dissolved in ethyl acetate, washed with water, and dried. The solvent is evaporated away, and the resulting residue is crystallized from ether. The crystal formed is collected and dried to obtain 3-(2,4-dichlorobenzyl)-5-(1-pentanesulfonylcarbamoyl)indole (88) (0.258 g).

Workup

  1. stirringstirred at 100° C. for 40 hours
  2. temperatureThe reaction mixture is cooled
  3. additionadded
  4. customThen, the gummy residue formed
  5. customis collected
  6. dissolutionThis is dissolved in ethyl acetate
  7. washwashed with water
  8. customdried
  9. customThe solvent is evaporated away
  10. customthe resulting residue is crystallized from ether
  11. customThe crystal formed
  12. customis collected
  13. customdried

Sources & evidence

ORD record
ord-5ca32dcb8ef74ebdabc8e6456179bc47
Source dataset
uspto-grants-2002_06
Patent number
US06410584B1

Reaction notes

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