Sodium hydride → HCID 74423574, compound

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Reaction Steps

To 3,6,6,-trimethyl-1,5,6,7-tetrahydro-indol-4-one (0.104 g, 1.4 eq) in dimethylacetamide (3 mL), sodium hydride (14.4 mg, 1.4 eq) is added slowly and stirred at RT for 0.5 h. Then 1-(1-amino-6-fluoro-isoquinolin-4-yl)-ethanone oxime (90 mg, 1 eq) is added and the mixture is stirred at 150° C. overnight. The reaction is poured into Sat'd NH4Cl aq. (200 mL), extracted by EtOAc (3×100 mL), dried over Na2SO4, filtered, concentrated to give a crude product. That is purified by Biotage chromatography, eluted by 20% MeOH in DCM to give 1-(1-amino-4-(1-(hydroxyimino)ethyl)isoquinolin-6-yl)-3,6,6-trimethyl-6,7-dihydro-1H-indol-4(5H)-one (20 mg, 13%). LC/MS m/z=377 [M+H]+.

Provenance & Evidence