(4-Methoxy-2-methylphenyl)boronic acid → (+/-)-trans 2-(4-methoxy-2-methylphenyl)-5,6,8,8a,9,10,11,11a-octahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline

HRID 1836575Notes

Reaction equation

HRID 1836575 reaction equation
CC1C=C(OC)C=CC=1B(O)O.Cl.Cl.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[C:25]3[C:30]4=[C:31]([CH2:33][CH2:34][CH2:35][N:29]4[CH2:28][C@@H:27]4[CH2:36][NH:37][CH2:38][C@@H:26]34)[CH:32]=2)=[C:19]([C:39](F)(F)F)[CH:18]=1>>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[C:25]3[C:30]4=[C:31]([CH2:33][CH2:34][CH2:35][N:29]4[CH2:28][C@@H:27]4[CH2:36][NH:37][CH2:38][C@@H:26]34)[CH:32]=2)=[C:19]([CH3:39])[CH:18]=1

Participants

3

Reactant 2

HCID 2773486(4-Methoxy-2-methylphenyl)boronic acidHCID 131724531(+/-)-trans-2-[4-methoxy-2-(trifluoromethyl)phenyl]-5,6,8,8a,9,10,11,11a-octahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline, bis-hydrochloride salt

Product 1

HCID 60088318(+/-)-trans 2-(4-methoxy-2-methylphenyl)-5,6,8,8a,9,10,11,11a-octahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline

Procedure

Using 2-methyl-4-methoxyphenyl boronic acid and following procedures described in EXAMPLE 34, (±)-trans tert-butyl 2-bromo-5,6,8a,9,11,11a-hexahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline-10(8H)-carboxylate from EXAMPLE 7, Part A was converted into the title compound of EXAMPLE 36 as a yellow semi-solid. 1H NMR (500 MHz, CDCl3) δ 1.26 (s, 1H), 1.95 (m, 1H), 2.01 (m, 1H), 2.16 (m, 1H), 2.28 (s, 3H), 2.70-2.90 (m, 4H), 2.98 (t, 1H, J=7 Hz), 3.22 (m, 1H), 3.30 (m, 4H), 3.38 (t, 1H, J=7 Hz), 3.60 (s, 3H), 6.58 (s, 1H), 6.74 (d, 1H, J=8.4 Hz), 6.77 (s, 2H), 7.12 (d, 1H, J=8.4 Hz). LRMS (ES)+: 335 (M+H)+.

Sources & evidence

ORD record
ord-935fa4d5becd407297d127171635a5d8
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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