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

HRID 490829Notes

Reaction equation

HRID 490829 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[CH3:11].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[CH:17]=O.[C:24](#[N:28])[CH2:25][C:26]#[N:27]>>[NH2:28][C:24]1[O:1][C:2]2[C:10]([CH:17]([C:16]3[CH:15]=[C:14]([O:13][CH3:12])[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=3)[C:25]=1[C:26]#[N:27])=[CH:9][CH:8]=[C:7]1[N:6]([CH3:11])[CH:5]=[CH:4][C:3]=21

Participants

4

Reactant 3

HCID 8010MalononitrileHCID 817473,5-DimethoxybenzaldehydeHCID 158257394-Hydroxy-1-methylindole

Product 1

HCID 104286592-Amino-3-cyano-4-(3,5-dimethoxyphenyl)-7-methyl-4H-pyrrolo[2,3-h]chromene

Procedure

The title compound was prepared from 4-hydroxy-1-methylindole (40 mg, 0.27 mmol), 3,5-dimethoxybenzaldehyde (45 mg, 0.27 mmol) and malononitrile (18 mg, 0.27 mmol) similar to Example 24 to yield 62 mg (60%) of white solids. 1H NMR (CDCl3): 7.04-7.00 (m, 2H), 6.81 (d, J=8.4 Hz, 1H), 6.55 (d, J=3.0 Hz, 1H), 6.37-6.31 (m, 3H), 4.77 (s, 1H), 4.64 (brs, 2H), 3.77-3.74 (m, 9H).

Sources & evidence

ORD record
ord-c0f873d5bb624d649fc94db6fca1ded5
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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