1-Pyrrolidineethanol → 4-(4-Fluoro-2-methylindol-5-yloxy)-6-methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)cinnoline

HRID 2180147Notes

Reaction equation

HRID 2180147 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([OH:24])=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[N:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:25])[NH:6]2.O[CH2:27][CH2:28][N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>>[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:27][CH2:28][N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[N:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:25])[NH:6]2

Participants

3

Reactant 2

HCID 762881-PyrrolidineethanolHCID 1357497764-(4-Fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxycinnoline

Product 1

HCID 224900194-(4-Fluoro-2-methylindol-5-yloxy)-6-methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)cinnolineYield 12%

Procedure

Using an analogous procedure to that described in Example 15, 4-(4-fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxycinnoline (0.2 g, 0.6 mmol), (prepared as described in Example 4), was reacted with 1-(2-hydroxyethyl)pyrrolidine (0.11 ml, 0.9 mmol) to give 4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)cinnoline (30 mg, 12%).

Sources & evidence

ORD record
ord-7fd0df57568c45a2bb0401099aafb785
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

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