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

HRID 490826Notes

Reaction equation

HRID 490826 reaction equation
[C:1]([O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([CH:13]=O)=[CH:7][C:6]=1[Br:15])(=[O:3])[CH3:2].[C:16](#[N:20])[CH2:17][C:18]#[N:19].[OH:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=[CH:25][N:26]2[CH3:31]>C(O)C>[NH2:19][C:18]1[O:21][C:22]2[C:30]([CH:13]([C:8]3[CH:9]=[C:10]([O:11][CH3:12])[C:5]([O:4][C:1](=[O:3])[CH3:2])=[C:6]([Br:15])[CH:7]=3)[C:17]=1[C:16]#[N:20])=[CH:29][CH:28]=[C:27]1[N:26]([CH3:31])[CH:25]=[CH:24][C:23]=21

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 20639262-Bromo-4-formyl-6-methoxyphenyl AcetateHCID 158257394-Hydroxy-1-methylindole

Product 1

HCID 103223672-Amino-4-(4-acetoxy-3-bromo-5-methoxyphenyl)-3-cyano-7-methyl-4H-pyrrolo[2,3-h]chromeneYield 5.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-bromo-4-formyl-6-methoxyphenyl acetate (273 mg, 1 mmol) and malononitrile (66 mg, 1 mmol) in 10 mL of ethanol was added 4-hydroxy-1-methylindole (147 mg, 1 mmol) and the solution was stirred at room temperature overnight. The solvent was removed in vacuo. The crude material was purified by column chromatography (2:1, hexane:ethyl acetate) to yield 25 mg (5.3%) of the title compound 1H NMR (CDCl3): 7.07-7.04 (m, 2H), 6.92 (s, 1H), 6.79-6.77 (m, 2H), 6.57 (s, 1H), 4.81 (s, 1H), 4.70 (s, 2H), 3.79 (s, 6H), 2.34 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude material was purified by column chromatography (2:1, hexane:ethyl acetate)

Sources & evidence

ORD record
ord-ee21c31e8c434e5c8c98e39150aee006
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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