Malononitrile → HCID 10345146, compound

HRID 490823Notes

Reaction equation

HRID 490823 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[C:9]([C:10](C)([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Br:24])[CH:15]=3)[C:11]=1[C:12]#[N:13])=[CH:8][CH:7]=[C:6]1[N:26](C3CO3)[CH:27]=[CH:28][C:5]=21.[O:32]1[CH2:34][CH:33]1[CH2:35]N1C2C(=C(O)C=CC=2)C=C1.BrC1C(OC)=C(OC)C=C(C=1)C=O.C(#N)CC#N.N1CCCCC1>>[NH2:1][C:2]1[O:3][C:4]2[C:9]([CH:10]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Br:24])[CH:15]=3)[C:11]=1[C:12]#[N:13])=[CH:8][CH:7]=[C:6]1[N:26]([CH2:35][CH:33]3[CH2:34][O:32]3)[CH:27]=[CH:28][C:5]=21

Participants

6

Reactant 5

HCID 8010MalononitrileHCID 8082PiperidineHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 85887666HCID 85887666, compoundHCID 86604976HCID 86604976, compound

Product 1

HCID 10345146HCID 10345146, compound

Procedure

2-Amino-4-(3-bromo-4,5-dimethoxyphenyl)-3-cyano-7-oxiranyl-methyl-4H-pyrrolo[2,3-h]chromene: The title compound was prepared from 1-oxiranylmethyl-4-hydroxy-indole (70 mg, 0.37 mmol), 5-bromoveratraldehyde (91 mg, 0.37 mmol), malononitrile (25 mg, 0.37 mmol) and piperidine (0.01 mL, 0.18 mmol), similar to Example 16, to yield 80 mg (45%) of a white solid. 1H NMR (CDCl3): 7.15 (dd, J=1.5 Hz, 1H), 7.10 (dd, J=2.7 Hz, 1H), 6.92-6.91 (m, 1H), 6.78-6.75 (m, 2H), 6.62 (dd, J=0.9 Hz, 1H), 4.77 (s, 1H), 4.70 (brs, 2H), 4.48-4.43 (m, 1H), 4.15-4.13 (m, 1H), 3.83 (s, 3H), 3.82 (s, 3H), 3.28-3.27 (m, 1H), 2.84-2.81 (m, 1H), 2.48-2.44 (m, 1H).

Sources & evidence

ORD record
ord-a28beba0885d49f5a98253ed10d9b088
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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