HuagongsheHuagongshe Chemistry Print Report · For research reference only
(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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (4-Methoxy-2-methylphenyl)boronic acid | HCID 2773486 | — |
| Reactant | (+/-)-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 | HCID 131724531 | — |
| Product | (+/-)-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 | HCID 60088318 | — |
Reaction Steps
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)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06777406B2 |
| Source dataset | uspto-grants-2004_08 |
| ORD ID | ord-935fa4d5becd407297d127171635a5d8 |
| Source note | uspto-grants-2004_08 |