Hydrochloric Acid → HCID 19085541, compound

HRID 962764Notes

Reaction equation

HRID 962764 reaction equation
[OH:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:9]=2)=[O:7])=[CH:4][C:3]=1[O:28][CH2:29][CH2:30][CH2:31][Cl:32].Br[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][O:1][C:2]2[CH:27]=[CH:26][C:5]([C:6]([C:8]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]([S:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH:9]=3)=[O:7])=[CH:4][C:3]=2[O:28][CH2:29][CH2:30][CH2:31][Cl:32])=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7721p-Xylyl bromideHCID 11430Potassium CarbonateHCID 19085567HCID 19085567, compound

Product 1

HCID 19085541HCID 19085541, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[4-Hydroxy-3-(3-chloropropoxy)benzoyl]-1-(phenylsulfonyl)indole (0.72 g) obtained in Step 1 was dissolved in N,N-dimethylformamide (7 ml). α-bromo-p-xylene (0.37 g) and potassium carbonate (0.28 g) were added to the resultant solution and stirred for 2 hours at room temperature. 2N HCl was added to the reaction mixture, followed by extraction with ethyl acetate. The resultant extract was sequentially washed with saturated sodium bicarbonate solution and brine and then dried. The solvent was distilled off. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), obtaining 0.49 g of 3-[4-(4-methylphenylmethoxy)-3-(3-chloropropoxy)benzoyl]-1-(phenylsulfonyl)indole as a yellow oily substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. extractionThe resultant extract
  3. washwas sequentially washed with saturated sodium bicarbonate solution and brine
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-253ae01aa6224500911ff867bd2f53af
Source dataset
uspto-grants-1998_06
Patent number
US05760040

Reaction notes

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