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

HRID 490817Notes

Reaction equation

HRID 490817 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.[OH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][N:15]2[CH3:20].[C:21](#[N:25])[CH2:22][C:23]#[N:24].N1CCCCC1>>[NH2:25][C:21]1[O:10][C:11]2[C:19]([CH:8]([C:4]3[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=3)[C:22]=1[C:23]#[N:24])=[CH:18][CH:17]=[C:16]1[N:15]([CH3:20])[CH:14]=[CH:13][C:12]=21

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 158257394-Hydroxy-1-methylindole

Product 1

HCID 103176832-Amino-4-(5-bromo-pyridin-3-yl)-3-cyano-7-methyl-4H-pyrrolo [2,3-h]chromene

Procedure

The title compound was prepared from 5-bromo-pyridine-3-carbaldehyde (44 mg, 0.24 mmol), 4-hydroxy-1-methyl-indole (35 mg, 0.24 mmol), malononitrile (16 mg, 0.24 mmol) and piperidine (0.05 mL), similar to Example 10, and isolated as a solid. 1H NMR (CDCl3): 8.54 (d, J=2.4 Hz, 1H), 8.47 (d, J=1.8 Hz, 1H), 7.60 (m, 1H), 7.08 (d, J=3.0 Hz, 1H), 7.05 (d, J=8.4 Hz, 1H), 6.70 (d, J=8.7 Hz, 1H), 6.58 (d, J=3.0 Hz, 1H), 4.89 (s, 1H), 4.78 (brs, 2H), 3.79 (s, 3H).

Workup

  1. customisolated as a solid

Sources & evidence

ORD record
ord-0fde72ed99914ef0be9c601c17284032
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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