2,6-Dimethylaniline → HCID 21056594, compound

HRID 2215900Notes

Reaction equation

HRID 2215900 reaction equation
C(OC([N:8]1[CH2:25][CH2:24][C@@H:11]2[N:12]([CH3:23])[C:13]3[C:14]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:16]=[CH:17][C:18]=3[C@H:10]2[CH:9]1Br)=O)(C)(C)C.[CH3:27][C:28]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:29]=1[NH2:30]>>[CH3:27][C:28]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:29]=1[NH:30][C:16]1[CH:15]=[C:14]([C:19]([F:21])([F:22])[F:20])[C:13]2[N:12]([CH3:23])[C@H:11]3[CH2:24][CH2:25][NH:8][CH2:9][C@H:10]3[C:18]=2[CH:17]=1

Participants

3

Reactant 2

HCID 68962,6-DimethylanilineHCID 67182044HCID 67182044, compound

Product 1

HCID 21056594HCID 21056594, compound

Procedure

The title compound was prepared by following the general coupling procedure as a yellow solid (18 mg, 50%) from (4aS,9bR)-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 2,6-dimethylaniline (39 mg, 0.30 mmol). 1H NMR (CDCl3, 300 MHz) δ (ppm) 1.87–1.98 (m, 2H), 2.20 (s, 6H), 2.30–2.70 (m, 3H), 2.78–3.20 (m, 6H), 3.33–3.45 (m, 1H), 5.07 (s, 1H), 6.46 (d, J=2.2 Hz, 1H), 6.59 (d, J=2.2 Hz, 1H), 7.00–7.18 (m, 3H).

Sources & evidence

ORD record
ord-993c069353404ed28d091bafdea6ea6c
Source dataset
uspto-grants-2006_09
Patent number
US07109339B2

Reaction notes

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