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

HRID 490816Notes

Reaction equation

HRID 490816 reaction equation
[CH3:1][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>C(O)C>[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]([CH3:1])[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

6

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 141411585-Methylpyridine-3-carbaldehydeHCID 158257394-Hydroxy-1-methylindole

Product 1

HCID 100186402-Amino-3-cyano-4-(5-methyl-pyridin-3-yl)-7-methyl-4H-pyrrolo[2,3-h]chromene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-methyl-pyridine-3-carbaldehyde (121 mg, 1 mmol) and 4-hydroxy-1-methyl-indole (146 mg, 0.99 mmol) in absolute ethanol (5 mL) at 0° C., was added malononitrile (67 mg, 1.01 mmol) and piperidine (0.1 mL). The clear solution was slowly warmed to room temperature and stirred overnight. The product was collected by vacuum filtration, washed with ethanol, and dried in vacuo as a yellow powder (269 mg, 86%). 1H NMR (CDCl3): 8.34 (d, J=2.1 Hz, 1H), 8.31 (dd, J=0.6, 2.1 Hz, 1H), 7.29 (m, 1H), 7.06 (d, J=3.0 Hz, 1H), 7.02 (dd, J=0.9, 8.4 Hz, 1H), 6.72 (d, J=8.4 Hz, 1H), 6.57 (dd, J=0.9, 3.0 Hz, 1H), 4.85 (s, 1H), 4.72 (brs, 2H), 3.77 (s, 3H), 2.27 (s, 3H).

Workup

  1. filtrationThe product was collected by vacuum filtration
  2. washwashed with ethanol
  3. dry with materialdried in vacuo as a yellow powder (269 mg, 86%)

Sources & evidence

ORD record
ord-5928ae2aaf4b4760ac627915061d2db0
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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