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Dimethylformamide → 3-Methoxycarbonylvinylcarbazole

HRID 448515
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HRID 448515 반응식
CN(C=O)C.I[C:7]1[CH:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3.C(N(CCCC)CCCC)CCC.[C:33]([O:37][CH3:38])(=[O:36])[CH:34]=[CH2:35]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:38][O:37][C:33]([CH:34]=[CH:35][C:7]1[CH:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:36]
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참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 7294Methyl AcrylateHCID 7622TributylamineHCID 36780693-iodo-9H-carbazole2회

생성물 1

HCID 668960893-Methoxycarbonylvinylcarbazole수율 62%

시약·촉매·용매 2

HCID 167845palladium(II) acetate
촉매
HCID 962Water용매

실험 절차

To a DMF solution (0.25 mL) of palladium acetate (38.0 mg, 0.17 μmol), compound (1) (0.50 g, 1.71 mmol) as well as tributylamine (0.41 μL, 1.71 mmol), methyl acrylate (0.38 L, 4.27 mmol) and H2O (1.0 mL) were added in this order. The reaction solution was allowed to react for 10 minutes at 160° C. using microwaves, and the reaction was traced by TLC to confirm the disappearance of compound (1). The palladium powder was removed by Kiriyama filtration, and then the residue was purified by column chromatography (HexH:AcOEt=3:1). Thus, compound (7) (0.26 g, 62%) was obtained as a white powder.

후처리

  1. customto react for 10 minutes at 160° C.
  2. customThe palladium powder was removed by Kiriyama filtration
  3. customthe residue was purified by column chromatography (HexH:AcOEt=3:1)

출처 및 근거

ORD 기록
ord-570aca7291c54e3395455cea8e0bcd9f
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481714B2

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