Malononitrile → HCID 11740484, compound

HRID 490831Notes

Reaction equation

HRID 490831 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH3:11].[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.[C:21](#[N:25])[CH2:22][C:23]#[N:24]>>[NH2:25][C:21]1[O:1][C:2]2[C:10]([CH:16]([C:15]3[CH:18]=[CH:19][CH:20]=[C:13]([Br:12])[CH:14]=3)[C:22]=1[C:23]#[N:24])=[CH:9][CH:8]=[C:7]1[N:6]([CH3:11])[CH:5]=[CH:4][C:3]=21

Participants

4

Reactant 3

HCID 8010MalononitrileHCID 765833-BromobenzaldehydeHCID 158257394-Hydroxy-1-methylindole

Product 1

HCID 11740484HCID 11740484, compound

Procedure

The title compound was prepared from 4-hydroxy-1-methylindole (40 mg, 0.27 mmol), 3-bromobenzaldehyde (48 mg, 0.27 mmol) and malononitrile (18 mg, 0.27 mmol) similar to Example 24 to yield 79 mg (80%) of white solids. 1H NMR (CDCl3): 7.36-7.31 (m, 2H), 7.21-7.16 (m, 2H), 7.06-7.01 (m, 2H), 6.73 (d, J=8.4 Hz, 1H), 6.57 (dd, J=3.0 Hz, J=0.9 Hz, 1H), 4.82 (s, 1H), 4.69 (brs, 2H), 3.78 (s, 3H).

Sources & evidence

ORD record
ord-bbd4ec50bc2a41bd870709cf64a76c41
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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