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

HRID 490833Notes

Reaction equation

HRID 490833 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[C:21]([O:22][CH3:23])=[CH:20][C:17]([CH:18]=O)=[CH:16][C:15]=1[I:24].[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:20]=[C:21]([O:22][CH3:23])[C:14]([O:13][CH3:12])=[C:15]([I:24])[CH:16]=3)[C:26]=1[C:27]#[N:28])=[CH:9][CH:8]=[C:7]1[N:6]([CH3:11])[CH:5]=[CH:4][C:3]=21

Participants

4

Reactant 3

HCID 8010MalononitrileHCID 27781133-Iodo-4,5-dimethoxybenzaldehydeHCID 158257394-Hydroxy-1-methylindole

Product 1

HCID 100511332-Amino-3-cyano-4-(4,5-dimethoxy-3-iodophenyl)-7-methyl-4H-pyrrolo[2,3-h]chromene

Procedure

The title compound was prepared from 4-hydroxy-1-methylindole (40 mg, 0.27 mmol), 4,5-dimethoxy-3-iodo-benzaldehyde (80 mg, 0.27 mmol) and malononitrile (18 mg, 0.27 mmol) similar to Example 24 to yield 91 mg (69%) of white solids. 1H NMR (CDCl3): 7.19 (d, J=1.8 Hz, 1H), 7.07-7.02 (m, 2H), 6.77-6.74 (m, 2H), 6.57 (d, J=3.3 Hz, 1H), 4.76 (s, 1H), 4.69 (brs, 2H), 3.81-3.78 (m, 9H).

Sources & evidence

ORD record
ord-ab9ee0f59f774cc2a9e9e34759b0ac2f
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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