Sodium Hydroxide → HCID 46898224, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 76 mg (0.133 mmol) of (RS, SR)-2-[(3-bromo-benzenesulfonyl)-fluoro-(5-methyl-[1,3,4]oxadiazol-2-yl)-methyl]-7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indole (example 106) in 1.5 mL of DMF was treated with 1 mg (0.005 mmol) of CuI, 37 mg (0.29 mmol) of DIPEA, 17 mg (0.015 mmol) of tetrakis(triphenylphosphine)palladium and 71 mg (0.72 mmol) of ethynyltrimethylsilane and the resulting suspension stirred at 80° C. during 4 hrs. Diluted aqueous NaOH was added and the mixture extracted twice with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and evaporated. Chromatography on silica gel with heptane/EtOAc (1:1) gave 33 mg (48%) of (RS, SR)-7-chloro-2-[(3-ethynyl-benzenesulfonyl)-fluoro-(5-methyl-[1,3,4]oxadiazol-2-yl)-methyl]-1,2,3,4-tetrahydro-cyclopenta[b]indole as a yellow solid, MS: 471 (MH+).

Provenance & Evidence