Ammonium thiocyanate → 6-tert-butyl-5-thiocyanato-1H-indole-2-carboxylic acid ethyl ester

HRID 1859570Notes

Reaction equation

HRID 1859570 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=2)=[O:5])[CH3:2].[S-:19][C:20]#[N:21].[NH4+].BrBr>CO>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([S:19][C:20]#[N:21])=[C:10]([C:15]([CH3:17])([CH3:16])[CH3:18])[CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 15666Ammonium thiocyanateHCID 24408BromineHCID 43415424Ethyl 6-(tert-Butyl)indole-2-carboxylate

Product 1

HCID 225727726-tert-butyl-5-thiocyanato-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared according to General Method 13 using 6-tert-butyl-1H-indole-2-carboxylic acid ethyl ester (prepared in Example YY; 3.5 g, 14 mmol), ammonium thiocyanate (1.63 g, 21.4 mmol), bromine (3.42 g, 21.4 mmol), and MeOH (50 mL). The crude product was purified by flash silica gel chromatography (5%-50% EtOAc in hexanes as eluents). MS(APCI): 301 (M−H).

Workup

  1. customThe crude product was purified by flash silica gel chromatography (5%-50% EtOAc in hexanes as eluents)

Sources & evidence

ORD record
ord-67f9ba560efb49dfb331dcb3ac2b4532
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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