Methyl iodide → HCID 86751462, compound

HRID 582642Notes

Reaction equation

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

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 178496862HCID 178496862, compound

Product 1

HCID 86751462HCID 86751462, compoundYield 25%

Procedure

A solution of methyl quindoline-11-carboxylate (0.16 g, 0.58 mmol) from Example 15 in methyl iodide (3 mL, 30.2 mmol) was stirred at rt for 48 hours. The excess of CH3I was removed in vacuo and the residue was washed thoroughly with diethyl ether to afford the 0.06 g (25.0%) of the title compound as a red solid, mp 246.5-247.0° C.; 1H NMR (DMSO-d6) δ 12.70 (s, 1H, NH), 8.92-8.80 (m, 3H), 8.22 (t, J=8.0, 1H), 8.09-7.95 (m, 2H), 7.94 (d, J=8.0, 1H), 7.58 (t, J=7.6, 1H); 13C NMR (DMSO-d6) δ 164.01, 146.47, 141.01, 135.35, 135.14, 132.10, 131.94, 128.40, 126.89, 126.37, 122.88, 122.09, 118.60, 113.86, 113.54, 95.02, 54.20, 41.29; MS (LSIMS, m/z) 291 (M+).

Workup

customThe excess of CH3I was removed in vacuo
washthe residue was washed thoroughly with diethyl ether

Sources & evidence

ORD record: ord-c0c4ccc52d4f404293cbebdda74c723e
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05925647

Reaction notes

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