Phenylmethanesulfonyl chloride → HCID 9874688, compound

HRID 1821459Notes

Reaction equation

HRID 1821459 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]([CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:6]2[C:11]([C:12]=1[CH2:13][CH2:14][O:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1)=[CH:10][C:9]([Cl:26])=[CH:8][CH:7]=2.C([O-])(O)=O.[Na+].[C:45]1([CH2:51][S:52](Cl)(=[O:54])=[O:53])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(Cl)Cl>[CH:27]([N:5]1[C:6]2[C:11](=[CH:10][C:9]([Cl:26])=[CH:8][CH:7]=2)[C:12]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:24][CH:25]=2)=[C:4]1[CH2:3][CH2:2][NH:1][S:52]([CH2:51][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)(=[O:54])=[O:53])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 74740Phenylmethanesulfonyl chlorideHCID 516892Sodium Bicarbonate2×HCID 16116212HCID 16116212, compound

Product 1

HCID 9874688HCID 9874688, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methyl 4-{2-[2-(2-aminoethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]ethoxy}benzoate (1.0 equiv) and sat. NaHCO3 (0.14 M) in CH2Cl2 (0.07 M) was added α-toluenesulfonyl chloride (1.0 equiv). After 1 h the mixture was poured into saturated sodium bicarbonate and extracted with CH2Cl2. The combined organic phase was washed with brine, dried over sodium sulfate and purified by column chromatography (gradient elution using 20% EtOAc-hexanes →50% EtOAc-hexanes) to afford 86% of the desired product.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. custompurified by column chromatography (gradient elution using 20% EtOAc-hexanes →50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-4b6246df63df4b8dbec86b3e06894b51
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

Loading…