Hydrochloric Acid → 6-Methoxy-1-(phenylsulfonyl)-1H-indol-5-ol

HRID 1159863Notes

Reaction equation

HRID 1159863 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH:13]=[CH:12]2)C1C=CC=CC=1.C1CCCCC=1.Cl>[Pd].CCO>[CH3:19][O:18][C:17]1[CH:16]=[C:15]2[C:11]([CH:12]=[CH:13][N:14]2[S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:10][C:9]=1[OH:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8079CyclohexeneHCID 18765369HCID 18765369, compound2×

Product 1

HCID 672416826-Methoxy-1-(phenylsulfonyl)-1H-indol-5-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To 5-(benzyloxy)-6-methoxy-1-(phenylsulfonyl)-1H-indole (6.6 g, 17 mmol; Intermediate 100) and Pd/C (2 g, 30 wt %), EtOH (30 mL), cyclohexene (9 mL) and HCl (9 mL) were added. The reaction mixture was warmed to 150° C. for 5 min using microwave heating. The Pd/C was filtered off and the solvent was removed under reduced pressure to afford the title compound in quantitative yield (5 g) as a black gum. The product was used without any further purification in the next step. MS (ESI+) for C15H13NO4S m/z 304 (M+H)+.

Workup

  1. temperatureheating
  2. filtrationThe Pd/C was filtered off
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9205d1c2b2ff4f5988c83285962cf3c0
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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