Ethyl iodoacetate → Ethyl 4-cyano-3-(4-methoxyphenyl)-5-morpholin-4-yl-2,3-dihydrothiophene-2-carboxylate

HRID 572605노트

반응식

HRID 572605 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]([C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[S:14])[C:11]#[N:12])=[CH:5][CH:4]=1.I[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].CCN(C(C)C)C(C)C>C(#N)C>[C:11]([C:10]1[CH:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:14][C:13]=1[N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)#[N:12]

참가 물질

5

반응물 3

HCID 12183Ethyl iodoacetateHCID 81531DiisopropylethylamineHCID 866375463-(4-Methoxyphenyl)-2-(morpholin-4-ylcarbonothioyl)acrylonitrile

생성물 1

HCID 68628637Ethyl 4-cyano-3-(4-methoxyphenyl)-5-morpholin-4-yl-2,3-dihydrothiophene-2-carboxylate수율 63%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 3-(4-methoxyphenyl)-2-(morpholin-4-ylcarbonothioyl)acrylonitrile (from step 1), ethyl iodoacetate (0.25 mL, 2.1 mmol) and DIPEA (0.5 mL, 2.9 mmol) was dissolved in ACN (2 mL) and subjected to MWI at 150° C. for 10 min. The mixture was allowed to cool and was concentrated. The residue was diluted with 5% sodium bisulfite solution and extracted with EtOAc. The organic solutions were combined, washed with sat NaHCO3 and brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give ethyl 4-cyano-3-(4-methoxyphenyl)-5-morpholin-4-yl-2,3-dihydrothiophene-2-carboxylate (0.168 g, 63% over two steps). LCMS: (AA) ES+ 375, ES− 373.

후처리

  1. temperatureto cool
  2. concentrationwas concentrated
  3. additionThe residue was diluted with 5% sodium bisulfite solution
  4. extractionextracted with EtOAc
  5. washwashed with sat NaHCO3 and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-49b4ce3181c742e383dc52f1851a3ccf
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029411B2

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