Malononitrile → 2-Amino-3-cyano-4-(3,5-dimethoxyphenyl)-7-hydroxymethyl-4H-pyrrolo [2,3-h]chromene

HRID 490836Notes

Reaction equation

HRID 490836 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH2:11][OH:12].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([O:23][CH3:24])[CH:22]=1)[CH:18]=O.[C:25](#[N:29])[CH2:26][C:27]#[N:28]>>[NH2:29][C:25]1[O:1][C:2]2[C:10]([CH:18]([C:17]3[CH:16]=[C:15]([O:14][CH3:13])[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=3)[C:26]=1[C:27]#[N:28])=[CH:9][CH:8]=[C:7]1[N:6]([CH2:11][OH:12])[CH:5]=[CH:4][C:3]=21

Participants

4

Reactant 3

HCID 8010MalononitrileHCID 817473,5-DimethoxybenzaldehydeHCID 247769031-(Hydroxymethyl)-1H-indol-4-ol

Product 1

HCID 102490092-Amino-3-cyano-4-(3,5-dimethoxyphenyl)-7-hydroxymethyl-4H-pyrrolo [2,3-h]chromene

Procedure

The title compound was prepared from 4-hydroxy-1-hydroxymethylindole (30 mg, 0.18 mmol), 3,5-dimethoxy-benzaldehyde (31 mg, 0.18 mmol) and malononitrile (12 mg, 0.18 mmol) similar to Example 24 to yield 19 mg (27%) of white solids. 1H NMR (CDCl3): 7.20-7.15 (m, 2H), 6.85 (d, J=8.1 Hz, 1H), 6.62 (d, J=3.3 Hz, 1H), 6.36-6.32 (m, 3H), 5.60 (s, 2H), 4.76 (s, 1H), 4.64 (brs, 2H), 3.75 (s, 6H), 2.43 (brs, 1H).

Sources & evidence

ORD record
ord-fa69b8e0d667425e8084c4ce78a62205
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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