4-fluoro-2-methyl-1H-indol-5-ol → HCID 10111016, compound

HRID 2222412Notes

Reaction equation

HRID 2222412 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:19][C:20]1[C:28]([OH:29])=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[C:23]([CH3:30])[NH:24]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][O:17][CH3:18])[N:5]=[CH:4][CH:3]=[C:2]2[O:29][C:28]1[C:20]([F:19])=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([CH3:30])=[CH:22]2)#[N:13]

Participants

4

Reactant 2

HCID 103520364-fluoro-2-methyl-1H-indol-5-olHCID 226465224-Chloro-6-cyano-7-(2-methoxyethoxy)quinoline

Product 1

HCID 10111016HCID 10111016, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using an analogous procedure to that described in Example 12, 4-chloro-6-cyano-7-(2-methoxyethoxy)quinoline (200 mg, 0.76 mmol) was reacted with 4-fluoro-5-hydroxy-2-methylindole (150 mg, 0.91 mmol), (prepared as described for the starting material in Example 11), in DMF (6 ml) to give 6-cyano-4-(4-fluoro-2-methylindol-5-yloxy)-7-(2-methoxyethoxy)quinoline (170 mg, 57%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-b76333d6e47f4a2aad91970af9fa25f0
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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