2-Methoxyaniline → (4aS,9bR)-(2-methoxylphenyl)-(5-methyl-6-trifluoromethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-8-yl)-amine

HRID 2215899Notes

Reaction equation

C(OC([N:8]1[CH2:26][CH2:25][C@@H:11]2[N:12]([CH3:24])[C:13]3[C:14]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:16](Br)=[CH:17][C:18]=3[C@@H:10]2[CH2:9]1)=O)(C)(C)C.[CH3:27][O:28][C:29]1[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=1[NH2:31]>>[O:28]([C:29]1[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=1[NH:31][C:16]1[CH:15]=[C:14]([C:20]([F:22])([F:23])[F:21])[C:13]2[N:12]([CH3:24])[C@H:11]3[CH2:25][CH2:26][NH:8][CH2:9][C@H:10]3[C:18]=2[CH:17]=1)[CH3:27]

Participants

Reactant 2

HCID 70002-Methoxyaniline

HCID 67182365(4aS,9bR)-8-bromo-5-methyl-6-trifluoromethyl-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester

Product 1

HCID 21056595(4aS,9bR)-(2-methoxylphenyl)-(5-methyl-6-trifluoromethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-8-yl)-amine

Procedure

The title compound was prepared by following the general coupling procedure as a yellow solid (22 mg, 61%) from (4aS,9bR)-8-bromo-5-methyl-6-trifluoromethyl-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester (Example 45, 41 mg, 0.095 mmol) and 2-methoxyaniline (37 mg, 0.30 mmol). 1H NMR (CDCl3, 300 MHz) δ (ppm) 1.82–2.00 (m, 2H), 2.58–2.80 (m, 3H), 2.80–3.00 (m, 5H), 3.07 (dd, J=12.9, 5.9 Hz, 1H), 3.15–3.25 (m, 1H), 3.45–3.55 (m, 1H), 3.91 (s, 3H), 5.97 (s, 1H), 6.75–6.90 (m, 3H), 6.99 (dd, J=1.6, 7.5 Hz, 1H), 7.09 (d, J=1.8 Hz, 1H).

Sources & evidence

ORD record: ord-c63109d8b6464d409a0db624405f68c0
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109339B2

Reaction notes

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