Potassium Carbonate → 1h-Indole-1-carboxylic acid,5-[(cyclohexylthio)methyl]-,1,1-dimethylethyl ester

HRID 2249905Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17]Cl)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:19]1([SH:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[NH4+].[Cl-]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][S:25][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 5-chloromethyl-indole-1-carboxylic acid tert-butyl ester (0.82 g, 3.10 mmol, 1.0 eq.), cyclohexyl mercaptan (0.53 mL, 1.4 eq.) and K2CO3 (0.90 g, 2.0 eq.) in DMF (6 mL) was heated at 40° C. until reaction completed. The reaction mixture was cooled to room temperature, diluted with sat. NH4Cl and extracted with diethyl ether. The organic extracts were dried over MgSO4, filtered and concentrated. The resulting mixture was purified by chromatography (5% EtOAc/hexanes) to give 5-cyclohexylsulfanylmethyl-indole-1-carboxylic acid tert-butyl ester (0.79 g, 74%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with diethyl ether
dry with materialThe organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe resulting mixture was purified by chromatography (5% EtOAc/hexanes)

Sources & evidence

ORD record: ord-7ec6f952b2524d0e89b4ce0e3e282347
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314936B2

Reaction notes

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