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

HRID 2215909Notes

Reaction equation

HRID 2215909 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.[NH2:27][C:28]1[C:29]([O:34][CH3:35])=[N:30][CH:31]=[CH:32][CH:33]=1.CC([O-])(C)C.[Na+]>>[CH3:35][O:34][C:29]1[C:28]([NH:27][C:16]2[CH:15]=[C:14]([C:20]([F:21])([F:22])[F:23])[C:13]3[N:12]([CH3:24])[C@H:11]4[CH2:25][CH2:26][NH:8][CH2:9][C@H:10]4[C:18]=3[CH:17]=2)=[CH:33][CH:32]=[CH:31][N:30]=1

Participants

4

Reactant 3

HCID 27374883-Amino-2-methoxypyridineHCID 23676156Sodium t-butoxideHCID 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 21056596(4aS,9bR)-(2-methoxy-pyridin-3-yl)-(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 Method A as a yellow solid (25 mg, 13%) 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, 217 mg, 0.5 mmol), 3-amino-2-methoxy-pyridine (186 mg, 1.5 mmol) and NaOt-Bu (144 mg, 1.5 mmol). MS (ESI): 379 (base, M+H).

Sources & evidence

ORD record
ord-530fa3e24b744bfe8c90ab2a337bea21
Source dataset
uspto-grants-2006_09
Patent number
US07109339B2

Reaction notes

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