Malononitrile → 2-Amino-4-(5-methyl-pyridin-3-yl)-3-cyano-7-methyl-8,9-dihydro-4H-pyrrolo[2,3-h]chromene

HRID 490838Notes

Reaction equation

HRID 490838 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[CH3:11].[CH3:12][C:13]1[CH:14]=[C:15]([CH:19]=O)[CH:16]=[N:17][CH:18]=1.[C:21](#[N:25])[CH2:22][C:23]#[N:24]>>[NH2:25][C:21]1[O:1][C:2]2[C:10]([CH:19]([C:15]3[CH:16]=[N:17][CH:18]=[C:13]([CH3:12])[CH:14]=3)[C:22]=1[C:23]#[N:24])=[CH:9][CH:8]=[C:7]1[N:6]([CH3:11])[CH2:5][CH2:4][C:3]=21

Participants

4

Reactant 3

HCID 8010MalononitrileHCID 141411585-Methylpyridine-3-carbaldehydeHCID 227261411H-Indol-4-ol, 2,3-dihydro-1-methyl-

Product 1

HCID 99731732-Amino-4-(5-methyl-pyridin-3-yl)-3-cyano-7-methyl-8,9-dihydro-4H-pyrrolo[2,3-h]chromene

Procedure

The title compound was prepared from 4-hydroxy-2,3-dihydro-1-methylindole (0.025 g, 0.17 mmol), 5-methyl-pyridine-3-carbaldehyde (0.020 g, 0.17 mmol), and malononitrile (0.011 g, 0.17 mmol) similar to Example 22 to yield 0.017 g (32%) of a white solid. 1H NMR (DMSO-d6): 8.31 (d, J=2.2 Hz, 1H), 8.27 (d, J=1.4 Hz, 1H), 7.37 (m, 1H), 6.71 (dd, J=8.0, 0.83 Hz, 1H), 6.25 (dd, J=8.0 Hz, 1H), 6.22 (brs, 2H), 4.68 (s, 1H), 3.36 (t, J=16.8 Hz, 2H), 2.94 (t, J=16.8 Hz, 2H), 2.70 (s, 3H).

Sources & evidence

ORD record
ord-bd210d8ffdee4c2fbeda834cf78c0de4
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

Loading…