Methyl iodide → Ethyl 5-methyl-6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

HRID 735199Notes

Reaction equation

[N+:1]([C:4]1[C:12]2[NH:11][C:10]3[CH2:13][CH2:14][N:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+].I[CH3:25]>COCCOC>[CH2:20]([O:19][C:17]([N:15]1[CH2:14][CH2:13][C:10]2[N:11]([CH3:25])[C:12]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=3[C:9]=2[CH2:16]1)=[O:18])[CH3:21]

Participants

Conditions

Temperature: 90 °C

Procedure

Ethyl 6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (0.33 g, 1.12 mmol) was combined with KOH (0.31 g, 5.6 mmol) and iodomethane (1.3 g, 8.96 mmol) in ethylene glycol dimethyl ether (5.6 mL) and stirred at 90° C. for 16 h. The inorganic solid was filtered and the filtrate evaporated to give ethyl-5-methyl-6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (0.37 g) as an orange oil in near quantitative yield. 1H NMR (CDCl3, 300 MHz) δ 7.74 (d, 1H, J=7.7 Hz), 7.67 (d, 1H, J=7.7 Hz), 7.12 (t, 1H, J=8.0 Hz), 4.70 (s, 2H), 4.22 (q, 2H, J=7.0 Hz), 3.91 (br. s, 2H), 3.62 (s, 3H), 2.84 (t, 2H, J=5.5 Hz), 1.30 (t, 3H, J=7.0 Hz) ppm.

Workup

filtrationThe inorganic solid was filtered
customthe filtrate evaporated

Sources & evidence

ORD record: ord-fbf902b1461f4a4a94b9f0239994f3b8
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592454B2

Reaction notes

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