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

HRID 490837Notes

Reaction equation

HRID 490837 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].[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([F:21])[CH:20]=1)[CH:16]=O.[C:22](#[N:26])[CH2:23][C:24]#[N:25]>>[NH2:26][C:22]1[O:1][C:2]2[C:10]([CH:16]([C:15]3[CH:14]=[C:13]([F:12])[CH:20]=[C:19]([F:21])[CH:18]=3)[C:23]=1[C:24]#[N:25])=[CH:9][CH:8]=[C:7]1[N:6]([CH3:11])[CH2:5][CH2:4][C:3]=21

Participants

4

Reactant 3

HCID 8010MalononitrileHCID 5881603,5-DifluorobenzaldehydeHCID 227261411H-Indol-4-ol, 2,3-dihydro-1-methyl-

Product 1

HCID 117247482-Amino-3-cyano-4-(3,5-difluorophenyl)-8,9-dihydro-7-methyl-4H-pyrrolo [2,3-h]chromene

Procedure

The title compound was prepared from 4-hydroxy-2,3-dihydro-1-methylindole (30 mg, 0.2 mmol), 3,5-difluoro-benzaldehyde (29 mg, 0.2 mmol) and malononitrile (13 mg, 0.2 mmol) similar to Example 22 to yield 20 mg (29%) of white solids. 1H NMR (CDCl3): 6.74-6.65 (m, 4H), 6.20 (d, J=7.8 Hz, 1H), 4.62 (s, 3H), 3.40 (t, J=8.1 Hz, 2H), 2.99 (t, J=8.7 Hz, 2H), 2.74 (s, 3H).

Sources & evidence

ORD record
ord-2247e38998e2476a958d9f5eb364be37
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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