4-fluoro-2-methyl-1H-indol-5-ol → 6-Cyano-4-(4-fluoro-2-methylindol-5-yloxy)-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline

HRID 2222409Notes

Reaction equation

HRID 2222409 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.[F:25][C:26]1[C:34]([OH:35])=[CH:33][CH:32]=[C:31]2[C:27]=1[CH:28]=[C:29]([CH3:36])[NH:30]2>CN(C=O)C>[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:35][C:34]1[C:26]([F:25])=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([CH3:36])=[CH:28]2)#[N:13]

Participants

4

Reactant 2

HCID 103520364-fluoro-2-methyl-1H-indol-5-olHCID 597122334-Chloro-6-cyano-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline

Product 1

HCID 101838876-Cyano-4-(4-fluoro-2-methylindol-5-yloxy)-7-(3-(4-methylpiperazin-1-yl)propoxy)quinolineYield 44.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using an analogous procedure to that described in Example 11, 4-chloro-6-cyano-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline (500 mg, 1.45 mmol) was reacted with 4-fluoro-5-hydroxy-2-methylindole (287 mg, 1.74 mmol), (prepared as described for the starting material in Example 11), in DMF (1 ml) to give 6-cyano-4-(4-fluoro-2-methylindol-5-yloxy)-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline (304 mg, 44%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-74f78843d08746f8893e3f3fa4fd0cfe
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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