Réaction #66070

ord-4326653e7c764e07903b871709a6edc9

Équation de réaction

C=Cc1ccc(C)nc1
product
C=Cc1ccc(C)nc1
2-methyl-5-vinylpyridine
Brc1ccc2[nH]c3c(c2c1)CN1CCC3CC1
product
Brc1ccc2[nH]c3c(c2c1)CN1CCC3CC1
9-bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole
Cc1ccc(/C=C/c2ccc3[nH]c4c(c3c2)CN2CCC4CC2)cn1
title compound
Cc1ccc(/C=C/c2ccc3[nH]c4c(c3c2)CN2CCC4CC2)cn1
9-[(E)-2-(6-methylpyridin-3-yl)vinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

The product of Example 1C (133 mg, 1.11 mmol) and the product of Example 8A (180 mg, 0.62 mmol) were processed as described in Example 1D to provide the title compound: 1H NMR (500 MHz, methanol-d4) δ ppm 2.03-2.14 (m, 4 H), 2.52 (s, 3 H), 2.98-3.04 (m, 1 H), 3.08 (dt, J=14.0, 6.9 Hz, 2 H), 3.20-3.29 (m, 2 H), 4.27 (s, 2 H), 7.05 (d, J=16.2 Hz, 1 H), 7.27 (d, J=8.2 Hz, 2 H), 7.33 (d, J=16.2 Hz, 1 H), 7.35-7.38 (m, 1 H), 7.49 (s, 1 H), 7.94 (dd, J=7.9, 2.1 Hz, 1 H), 8.50 (d, J=1.8 Hz, 1 H); MS (APCI) m/z 330 (M+H)+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08524703B2uspto-grants-2013_09