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

HRID 490818

반응식

HRID 490818 반응식
[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[C:14]([O:23][CH3:24])=[C:15]([O:21][CH3:22])[CH:16]=[C:17]([CH:20]=1)[CH:18]=O.[C:25](#[N:29])[CH2:26][C:27]#[N:28].N1CCCCC1>C(O)C>[NH2:29][C:25]1[O:1][C:2]2[C:10]([CH:18]([C:17]3[CH:16]=[C:15]([O:21][CH3:22])[C:14]([O:23][CH3:24])=[C:13]([Br:12])[CH:20]=3)[C:26]=1[C:27]#[N:28])=[CH:9][CH:8]=[C:7]1[N:6]([CH3:11])[CH:5]=[CH:4][C:3]=21

참가 물질

6

반응물 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 158257394-Hydroxy-1-methylindole

생성물 1

HCID 99329152-Amino-4-(3-bromo-4,5-dimethoxyphenyl)-3-cyano-7-methyl-4H-pyrrolo[2,3-h]chromene수율 66%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 4-hydroxy-1-methyl-indole (132 mg, 0.90 mmol), 5-bromoveratraldehyde (220 mg, 0.90 mmol) and malononitrile (59.3 mg, 0.90 mmol) in ethanol (3 mL) was added piperidine (0.05 mL, 0.45 mmol). The solution was stirred at room temperature for 2 h and precipitates were observed. The precipitates were collected by filtration and dried to yield 260 mg (66%) of title compound as a white solid. 1H NMR (CDCl3): 7.07-7.02 (m, 2H), 6.91(d, J=2.1 Hz, 1H), 6.77-6.75 (m, 2H), 6.57 (dd, J=0.9 Hz, 1H), 4.78 (s, 1H), 4.70 (brs, 2H), 3.82 (s, 6H), 3.78 (s, 3H).

후처리

  1. customprecipitates
  2. filtrationThe precipitates were collected by filtration
  3. customdried

출처 및 근거

ORD 기록
ord-6ee4917e5e4b46ee82f9243d2f45cbc2
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528164B2

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