1-hexyl-5-methoxy-2-methyl-1H-indole-3-acetamide → HCID 21191844, compound

HRID 1069596Notes

Reaction equation

HRID 1069596 reaction equation
B(Br)(Br)Br.C(Cl)Cl.[CH2:8]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([O:23]C)=[CH:20][CH:21]=2)[C:16]([CH2:25][C:26]([NH2:28])=[O:27])=[C:15]1[CH3:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>C(Cl)Cl.C(OCC)(=O)C>[CH2:8]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([OH:23])=[CH:20][CH:21]=2)[C:16]([CH2:25][C:26]([NH2:28])=[O:27])=[C:15]1[CH3:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 211918951-hexyl-5-methoxy-2-methyl-1H-indole-3-acetamideHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 21191844HCID 21191844, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1 mL of 1M BBr3/methylene chloride and 0.24 g (0.79 mmol) of 1-hexyl-5-methoxy-2-methyl-1H-indole-3-acetamide in 20 mL of methylene chloride as stirred for 16 hours, diluted with ethyl acetate and washed twice with water. The solution was dried (Na2SO4) and the solvent removed at reduced pressure to give 0.23 g of crude 1-hexyl-5-hydroxy-2-methyl-1H-indole-3-acetamide.

Workup

  1. washwashed twice with water
  2. dry with materialThe solution was dried (Na2SO4)
  3. customthe solvent removed at reduced pressure

Sources & evidence

ORD record
ord-ad8f6a5edda346ee995b5c5daa2d1faa
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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