2-Methyl-1H-indol-6-ol → HCID 22490038, compound

HRID 2180132Notes

Reaction equation

HRID 2180132 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20](Cl)=[CH:21][N:22]=[N:23]3)=[CH:18][C:17]=2[O:27][CH3:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:29][C:30]1[CH:38]=[C:37]2[C:33]([CH:34]=[C:35]([CH3:39])[NH:36]2)=[CH:32][CH:31]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([O:29][C:30]4[CH:38]=[C:37]5[C:33]([CH:34]=[C:35]([CH3:39])[NH:36]5)=[CH:32][CH:31]=4)=[CH:21][N:22]=[N:23]3)=[CH:18][C:17]=2[O:27][CH3:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 148785962-Methyl-1H-indol-6-olHCID 224900187-(1-Tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-chloro-6-methoxycinnoline

Product 1

HCID 22490038HCID 22490038, compound

Procedure

Using an analogous procedure to that described in Example 8, 7-(1-tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-chloro-6-methoxycinnoline (204 mg, 0.5 mmol) was reacted with 6-hydroxy-2-methylindole (100 mg, 0.55 mmol) to give 7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-6-methoxy-4-(2-methylindol-6-yloxy)cinnoline. The crude product was then treated with TFA to give 6-methoxy-4-(2-methylindol-6-yloxy)-7-(piperidin-4-ylmethoxy)cinnoline (10 mg, 4%).

Sources & evidence

ORD record
ord-1cd292265e54425e9738bd80b7c271c3
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

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