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Dimethylacetamide → Methyl 4-(3-cyanophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

HRID 601844
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HRID 601844 반응식
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:15]3[CH:14]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[NH:12][C:11]=3[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C[C:21]([N:23](C)C)=O>O.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:21]([C:2]1[CH:3]=[C:4]([CH:8]2[C:15]3[CH:14]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[NH:12][C:11]=3[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1)#[N:23]
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참가 물질

6

반응물 2

HCID 31374DimethylacetamideHCID 59180243Methyl 4-(3-bromophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

생성물 1

HCID 59180053Methyl 4-(3-cyanophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물
촉매
HCID 962Water용매

실험 절차

Methyl 4-(3-bromophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.103 g, 0.32 mmol) was combined with zinc cyanide (0.046 g, 0.39 mmol) and dissolved in dimethyl acetamide (3 mL). Then the solution was evacuated and back-flushed with N2 four times and sparged with N2 for an additional 5-10 min. Tetrakis(triphenylphosphine)palladium(0) (0.091 g, 0.08 mmol) was added and the reaction placed in a preheated (85° C.) heating block and stirred for 2 hour. The reaction was then cooled to room temperature and diluted with aqueous H2O (40 mL) and extracted three times with ethyl acetate. The organic layer was washed once with brine, then dried over Na2SO4. Purification by column chromatography (Isco CombiFlash) eluting with a gradient of 0-40% EtOAc/heptane afforded the title compound. 0.021 g. LCMS-MS (ESI+) 289.2 (M+Na).

후처리

  1. customThen the solution was evacuated
  2. customback-flushed with N2 four times
  3. customsparged with N2 for an additional 5-10 min
  4. customplaced in a preheated (85° C.)
  5. temperatureheating block
  6. extractionextracted three times with ethyl acetate
  7. washThe organic layer was washed once with brine
  8. dry with materialdried over Na2SO4
  9. customPurification by column chromatography (Isco CombiFlash)
  10. washeluting with a gradient of 0-40% EtOAc/heptane

출처 및 근거

ORD 기록
ord-2a4fc0b570b7464aa7fd8f347b9280da
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07902252B2

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