Ethyl 3-bromopropionate → Ethyl 3-[8-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]propanoate

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Reaction Steps

A mixture of 8-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine (Example 13) (0.036 g, 0.199 mmol), ethyl 3-bromopropanoate (0.084 g, 0.199 mmol) and DIPEA (0.097 ml, 0.557 mmol) was stirred and heated at 80° C. for 4 hours when a further portion of ethyl 3-bromopropanoate (0.084 g, 0.199 mmol) and DIPEA (0.097 ml, 0.557 mmol) were added and heated overnight when a further portion of ethyl 3-bromopropanoate (0.084 g, 0.199 mmol) and DIPEA (0.097 ml, 0.557 mmol) were added and heated for 3 more hours when all starting material gone. The cooled reaction mixture was diluted with EtOAc/water (30 ml of each) and the organics dried (magnesium sulphate), evaporated and purified by flash chromatography eluting with 1:1 EtOAc/iso-hexane to give the title compound (90 mgs) as a colourless gum. MS (ES) C25H2835ClN3O5 requires 485; found 486 [M+H]+.

Provenance & Evidence