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

HRID 490841Notes

Reaction equation

HRID 490841 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=O)[CH:6]=[N:7][CH:8]=1.[OH:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][N:16]2[CH3:21].[C:22](#[N:26])[CH2:23][C:24]#[N:25].N1CCCCC1>>[NH2:26][C:22]1[O:11][C:12]2[C:20]([CH:9]([C:5]3[CH:6]=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:23]=1[C:24]#[N:25])=[CH:19][CH:18]=[C:17]1[N:16]([CH3:21])[CH:15]=[CH:14][C:13]=21

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 109755495-Methoxy-3-pyridinecarboxaldehydeHCID 158257394-Hydroxy-1-methylindole

Product 1

HCID 102461722-Amino-3-cyano-4-(5-methoxy-pyridin-3-yl)-7-methyl-4H-pyrrolo[2,3-h]chromene

Procedure

The title compound was prepared from 5-methoxy-pyridine-3-carbaldehyde (70 mg, 0.51 mmol), 4-hydroxy-1-methylindole (75 mg, 0.51 mmol), malononitrile (34 mg, 0.51 mmol) and piperidine (0.05 ml, 0.5 mmol) similar to Example 1e to give 21 mg (12%) of white solids. 1H NMR (CDCl3): 8.19-8.15 (m, 2H), 7.07-6.99 (m, 3H), 6.73 (d, J=8.4 Hz, 1H), 6.57 (d, J=3.0 Hz, 1H), 4.89 (s, 1H), 4.75 (brs, 2H), 3.81-3.78 (m, 6H).

Sources & evidence

ORD record
ord-59a64c72a1934734a1a3343b6a6d961a
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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