HCID 57608295, compound → HCID 57608279, compound

HRID 1171216Notes

Reaction equation

HRID 1171216 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[C:13]3[C:9]([CH:10]=[C:11]([CH2:15][OH:16])[NH:12]3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1>[O-2].[O-2].[Mn+4].ClCCl>[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[C:13]3[C:9]([CH:10]=[C:11]([CH:15]=[O:16])[NH:12]3)=[CH:8][CH:7]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 57608295HCID 57608295, compound

Product 1

HCID 57608279HCID 57608279, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (5 mL) solution of (6-cyclopropylmethoxy-1H-indol-2-yl)-methanol (197 mg, 907 μmol) described in Production Example 73-1-3 was added manganese dioxide (789 mg, 9.07 mmol) at room temperature, which was stirred at room temperature for 17 hours. The reaction solution was filtered followed by concentrating the filtrate under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (144 mg, 74%) as a pale brown solid.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationby concentrating the filtrate under a reduced pressure
  3. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-2caa987c9b1d475aa4649af443df61cc
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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