HCID 86701547, compound → HCID 86701548, compound

HRID 2173980Notes

Reaction equation

HRID 2173980 reaction equation
[OH:1][CH2:2][C:3]1[C:11]([CH2:12][N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])=[CH:10][C:9]([CH3:24])=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[S:25]([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26]>C1(C)C=CC=CC=1.O=[Mn]=O>[O:23]=[C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21](=[O:22])[N:13]1[CH2:12][C:11]1[CH:10]=[C:9]([CH3:24])[C:8]2[N:7]([S:25]([C:28]3[CH:29]=[CH:30][C:31]([CH3:32])=[CH:33][CH:34]=3)(=[O:27])=[O:26])[CH:6]=[CH:5][C:4]=2[C:3]=1[CH:2]=[O:1]

Participants

4

Reactant 1

HCID 86701547HCID 86701547, compound

Product 1

HCID 86701548HCID 86701548, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 2-((4-(hydroxymethyl)-7-methyl-1-tosyl-1H-indol-5-yl)methyl)isoindoline-1,3-dione (180 mg, 0.38 mmol) and MnO2 (165 mg, 1.9 mmol) in toluene (20 mL) was stirred at 80° C. for 11 h. The reaction mixture was cooled to room temperature. The reaction mixture was filtered off through Celite®. The Celite® cake was washed with CH2Cl2. The combined filtrate was concentrated to give the title compound, with no need of further purification. MS (ESI+) m/z 473.1 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe reaction mixture was filtered off through Celite®
  3. washThe Celite® cake was washed with CH2Cl2
  4. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-0481adb9dc484dbeb7f391734a101f3c
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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