Allyl bromide → HCID 21906915, compound

HRID 1246946Notes

Reaction equation

HRID 1246946 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[CH3:12][C:13]([O-])(C)[CH3:14].[K+].C(Br)C=C>C1COCC1>[CH2:14]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1)[CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 138725-MethoxyindoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 21906915HCID 21906915, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Methoxyindole (294 mg, 2.0 mmol) was dissolved in THF (10 mL) and treated with 1M KOtBu in THF (2.2 mL, 2.2 mmol). After stirring for 1 hour, allyl bromide (190 μL, 2.2 mmol) was added and the reaction mixture was stirred for an additional 2 hrs. Standard aqueous workup provided N-Allyl-5-methoxyindole as an off white solid, which was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred for an additional 2 hrs

Sources & evidence

ORD record
ord-1b60c613f1d14ca88a7f510c4cdffa4d
Source dataset
uspto-grants-2006_10
Patent number
US07129250B2

Reaction notes

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