Iodoethane → HCID 71574639, compound

HRID 2369341Notes

Reaction equation

[CH3:1][C:2]1[N:17]2[C:5]([CH2:6][C:7]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[NH:9][C:8]=3[CH2:16]2)=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:3]=1[C:22]([O:24][CH3:25])=[O:23].[H-].[Na+].I[CH2:29][CH3:30]>>[CH2:29]([N:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[C:7]2[CH2:6][C:5]3[N:17]([CH2:16][C:8]1=2)[C:2]([CH3:1])=[C:3]([C:22]([O:24][CH3:25])=[O:23])[C:4]=3[C:18]([O:20][CH3:21])=[O:19])[CH3:30]

Participants

Reactant 3

HCID 6340Iodoethane

HCID 24758Sodium hydride

HCID 86690042HCID 86690042, compound

Product 1

HCID 71574639HCID 71574639, compound

Procedure

This compound was prepared from dimethyl 3-methyl-6,11-dihydro-5H-indolizino[6,7-b]indole-1,2-dicarboxylate (5.1 g, 15 mmol), NaH (0.54 g, 22.5 mmol) and iodoethane (2.3 g, 15 mmol). Yield 5.1 g (92%); mp 202-203° C. 1H NMR (DMSO-d6) δ 1.29 (3H, t, J=6.9 Hz, Me), 2.46 (3H, s, Me), 3.73 (3H, s, COOMe), 3.74 (3H, s, COOMe), 4.17 (2H, s, CH2), 4.20 (2H, q, J=6.9 Hz, CH2), 5.29 (2H, s, CH2), 7.05-7.09 (1H, m, ArH), 7.16-7.20 (1H, m, ArH), 7.49-7.51 (1H, m, ArH), 7.53-7.55 (1H, m, ArH). Anal. Calcd for (C21H22N2O4): C, 68.84; H, 6.05; N, 7.65. Found: C, 68.46; H, 6.06; N, 7.59.

Sources & evidence

ORD record: ord-e13dec1103614075be04e120dc86b73e
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703951B2

Reaction notes

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