Methanol → 6-tert-Butyl-5-mercapto-1H-indole-2-carboxylic acid ethyl ester

HRID 1859571Notes

Reaction equation

HRID 1859571 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([S:15]C#N)=[C:10]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=2)=[O:5])[CH3:2].S.[Na].[BH4-].[Na+].CO>CC(O)=O>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([SH:15])=[C:10]([C:18]([CH3:19])([CH3:21])[CH3:20])[CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 225727726-tert-butyl-5-thiocyanato-1H-indole-2-carboxylic acid ethyl esterHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 697360196-tert-Butyl-5-mercapto-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared according to the general Method 14b using (6-tert-butyl-5-thiocyanato-1H-indole-2-carboxylic acid ethyl ester (prepared in Example ZZ; 0.25 g, 0.83 mmol), sodium hydrogen sulfide (0.13 g, 2.48 mmol), sodium borohydride (0.188 g, 4.98 mmol), MeOH (5 mL), and AcOH (1 mL). MS(APCI): 278 (M+H).

Sources & evidence

ORD record
ord-f1b78852efc14cfdbdaa77f534f3e209
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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