반응 #592920

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methyl 3-(2-methylpropylidene)-4-oxochroman-7-carboxylate

4-hydrazinyl-2-methylbenzonitrile hydrochloride

→

title compound

수율 52.0%

2-(4-cyano-3-methylphenyl)-3-isopropyl-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid

수율 52.0%

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후처리

1. 1
   workup.ADDITIONyellow solid, 196 mg, 0.523 mmol, 52% yield, approximately 7:1 mixture of cis

실험 절차

The title compound was prepared from methyl 3-(2-methylpropylidene)-4-oxochroman-7-carboxylate (Preparation 32; 260 mg, 1.0 mmol) and 4-hydrazinyl-2-methylbenzonitrile hydrochloride (Preparation 2; 275 mg, 1.5 mmol) according to Method B and Method C (yellow solid, 196 mg, 0.523 mmol, 52% yield, approximately 7:1 mixture of cis:trans diastereomers). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.12 (br. s., 1H), 7.93 (d, J=8.2 Hz, 1H), 7.58 (dd, J=8.2, 1.6 Hz, 1H), 7.55 (d, J=8.6 Hz, 1H), 7.46 (d, J=1.6 Hz, 1H), 7.21 (d, J=1.6 Hz, 1H), 7.09 (dd, J=8.6, 2.3 Hz, 1H), 4.76-4.86 (m, 2H), 4.42 (dd, J=13.1, 10.4 Hz, 1H), 4.02 (ddd, J=13.2, 10.6, 5.9 Hz, 1H), 2.42 (s, 3H), 2.06-2.17 (m, 1H), 0.83 (d, J=7.4 Hz, 3H), 0.81 (d, J=7.4 Hz, 3H). ES-MS m/z 376 (M+H).

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