HCID 12904513, compound → HCID 10924147, compound

HRID 2174042Notes

Reaction equation

HRID 2174042 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14])([O-])=O>CCOC(C)=O.[Pd]>[S:13]([N:8]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:4]([NH2:1])[C:5]=2[CH:6]=[CH:7]1)([C:16]1[CH:17]=[CH:18][C:19]([CH3:20])=[CH:21][CH:22]=1)(=[O:14])=[O:15]

Participants

4

Reactant 1

HCID 12904513HCID 12904513, compound

Product 1

HCID 10924147HCID 10924147, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 4-nitro-1-tosyl-1H-indole (20.2 g, 63.9 mmol) in EtOAc (639 mL) was added 10% Pd/C (6.80 g, 6.39 mmol) and the mixture was stirred under hydrogen. After 4 hours the reaction was filtered through Celite®, rinsing with EtOAc. The filtrate was concentrated and purified by flash chromatography (0-70% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 287.1 (M+H).

Workup

  1. filtrationAfter 4 hours the reaction was filtered through Celite®
  2. washrinsing with EtOAc
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography (0-70% EtOAc in heptanes)

Sources & evidence

ORD record
ord-fb5c16ee9d6842f3aa92fa451c7471bf
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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