2,3-Dimethyl-1H-indol-5-ol → 6-Cyano-4-(2,3-dimethylindol-5-yloxy)-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline

HRID 2222424Notes

Reaction equation

HRID 2222424 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:25][C:26]1[NH:27][C:28]2[C:33]([C:34]=1[CH3:35])=[CH:32][C:31]([OH:36])=[CH:30][CH:29]=2>>[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1)[N:5]=[CH:4][CH:3]=[C:2]2[O:36][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26]([CH3:25])=[C:34]2[CH3:35])#[N:13]

Participants

3

Reactant 2

HCID 220307882,3-Dimethyl-1H-indol-5-olHCID 597122334-Chloro-6-cyano-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline

Product 1

HCID 101836246-Cyano-4-(2,3-dimethylindol-5-yloxy)-7-(3-(4-methylpiperazin-1-yl)propoxy)quinolineYield 70.7%

Procedure

Using an analogous procedure to that described in Example 20, 4-chloro-6-cyano-7-(3-(4methylpiperazin-1-yl)propoxy)quinoline (150 mg, 0.44 mmol), (prepared as described for the starting material in Example 12), was reacted with 2,3-dimethyl-5-hydroxyindole (84 mg, 0.52 mmol), (Arch. Pharm. 1972, 305, 159), to give 6-cyano-4-(2,3-dimethylindol-5-yloxy)-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline (146 mg, 60%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-29ac4b817e15491fbe0936dadb64436f
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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