HCID 59497564, compound → HCID 59497334, compound

HRID 1747449Notes

Reaction equation

HRID 1747449 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][OH:12])[CH:10]=1)[N:7]([CH3:13])[CH:6]=[CH:5]2>CC(C)=O.O=[Mn]=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]=[O:12])[CH:10]=1)[N:7]([CH3:13])[CH:6]=[CH:5]2

Participants

4

Reactant 1

HCID 59497564HCID 59497564, compound

Product 1

HCID 59497334HCID 59497334, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of (5-Bromo-1-methyl-1H-indol-7-yl)-methanol (220 mg, 0.92 mmol) in acetone (20 mL) was added MnO2 (239 mg, 2.7 mmol) at room temperature. The mixture was stirred at the same temperature for 3 hours. The solution was filtered and the filtrate was concentrated. The residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent to afford the desirable product 5-Bromo-1-methyl-1H-indole-7-carbaldehyde (177 mg, 81%) as a white solid.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-4971af24fd8846c2940cac42d1e6ba46
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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