1-[5-Methoxy-2-nitro-4-[3-(1-pyrrolidinyl)propoxy]phenyl]cyclobutanecarbonitrile → HCID 76332101, compound

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Reaction Steps

2-(4-(3-cyclopentylpropoxy)-5-methoxy-2-nitrophenyl)-2-methylpropanenitrile (0.126 g, 0.365 mmol), from Step 3, was treated in a manner analogous to that described for 1-(5-methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)phenyl)cyclobutanecarbonitrile in Step 5 of Example 7. Purification of the crude product by flash chromatography (silica gel, 10-30% MeOH/DCM) afforded 43 mg (37%) of 6-(3-cyclopentylpropoxy)-5-methoxy-3,3-dimethyl-3H-indol-2-amine 1H NMR (400 MHz, DMSO) δ 7.20 (s, 1H), 6.80 (s, 1H), 3.93 (t, J=6.5 Hz, 2H), 3.75 (s, 3H), 1.84-1.67 (m, 6H), 1.62-1.54 (m, 2H), 1.53-1.48 (m, 2H), 1.48-1.44 (m, 5H), 1.43-1.40 (m, 2H), 1.14-1.02 (m, 2H). MS (ESI) m/z 317 (M+H)+.

Provenance & Evidence