1H-indol-4-ol → HCID 69507081, compound

HRID 1768412Notes

Reaction equation

HRID 1768412 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([C:15]#[N:16])=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)[CH3:2].O[C:19]1C=C[CH:25]=[C:24]2[C:20]=1[CH:21]=[CH:22][NH:23]2>>[C:15]([CH:5]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=2)=[C:19]2[C:1](=[C:2]3[CH:25]=[CH:24][N:23]=[C:22]3[CH:21]=[CH:20]2)[O:3][C:4]1=[O:17])#[N:16]

Participants

3

Reactant 2

HCID 754211H-indol-4-olHCID 3674973-(3-methoxyphenyl)-2-cyano-acrylic acid ethyl ester

Product 1

HCID 69507081HCID 69507081, compound

Procedure

Alternatively, compounds of Formula III can be prepared as shown in Schemes 3 and 4. Condensation of 3,5-dimethoxybenzaldehyde with ethyl cyanoacetate in the presence of a base such as piperidine produces the 3-(3,5-dimethoxyphenyl)-2-cyano-acrylic acid ethyl ester. Treatment of the ester with 3-methoxyphenol in the presence of NaH produces the 3-cyano-7-methoxy-4-(3,5-dimethoxyphenyl)-2-oxo-2H-chromene. Similarly, reaction of 3-(3-methoxy-phenyl)-2-cyano-acrylic acid ethyl ester with 4-hydroxyindole produces 3-cyano-4-(3-methoxyphenyl)-2-oxo-2H-pyrrolo[2,3-h]chromene.

Sources & evidence

ORD record
ord-410630d26ea548d3a7c6624d40009807
Source dataset
uspto-grants-2007_06
Patent number
US07235674B2

Reaction notes

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