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

HRID 490835Notes

Reaction equation

HRID 490835 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:25][CH3:26])[C:22]=1[O:23][CH3:24])[CH:18]=O.[C:27](#[N:31])[CH2:28][C:29]#[N:30]>>[NH2:31][C:27]1[O:1][C:2]2[C:10]([CH:18]([C:17]3[CH:16]=[C:15]([O:14][CH3:13])[C:22]([O:23][CH3:24])=[C:21]([O:25][CH3:26])[CH:20]=3)[C:28]=1[C:29]#[N:30])=[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 68583,4,5-TrimethoxybenzaldehydeHCID 8010MalononitrileHCID 247769031-(Hydroxymethyl)-1H-indol-4-ol

Product 1

HCID 100243582-Amino-3-cyano-4-(3,4,5-trimethoxyphenyl)-7-hydroxymethyl-4H-pyrrolo[2,3-h]chromene

Procedure

The title compound was prepared from 4-hydroxy-1-hydroxymethylindole (30 mg, 0.18 mmol), 3,4,5-trimethoxy-benzaldehyde (36 mg, 0.18 mmol) and malononitrile (12 mg, 0.18 mmol) similar to Example 24 to yield 63 mg (84%) of white solids. 1H NMR (CDCl3): 7.21-7.20 (m, 2H), 6.84 (d, J=8.4 Hz, 1H), 6.64 (d, J=3.0 Hz, 1H), 6.42 (s, 2H), 5.61 (d, J=6.0 Hz, 2H), 4.78 (s, 1H), 4.67 (brs, 2H), 3.82-3.80 (m, 9H), 2.46 (brs, 1H).

Sources & evidence

ORD record
ord-30f654bcd7a94779b5f5da0e238dd8cc
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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