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Dichloromethane → 4-cyano-5-ethyl-1-methyl-3-{4-[1-methyl-2-(propane-2-sulfonylamino)-ethyl]-phenyl}-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 1865116
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HRID 1865116 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:24])[C:8]([CH2:22][CH3:23])=[C:9]([C:20]#[N:21])[C:10]=1B1OC(C)(C)C(C)(C)O1)=[O:5])[CH3:2].I[C:26]1[CH:31]=[CH:30][C:29]([CH:32]([CH3:41])[CH2:33][NH:34][S:35]([CH:38]([CH3:40])[CH3:39])(=[O:37])=[O:36])=[CH:28][CH:27]=1.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:24])[C:8]([CH2:22][CH3:23])=[C:9]([C:20]#[N:21])[C:10]=1[C:26]1[CH:27]=[CH:28][C:29]([CH:32]([CH3:41])[CH2:33][NH:34][S:35]([CH:38]([CH3:40])[CH3:39])(=[O:36])=[O:37])=[CH:30][CH:31]=1)=[O:5])[CH3:2]
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참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 222598982-(4-Iodophenyl) propyl isopropylsulfonamideHCID 579748024-cyano-5-ethyl-1-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid ethyl ester

생성물 1

HCID 690202154-cyano-5-ethyl-1-methyl-3-{4-[1-methyl-2-(propane-2-sulfonylamino)-ethyl]-phenyl}-1H-pyrrole-2-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Add 4-cyano-5-ethyl-1-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid ethyl ester (0.22 g, 0.65 mmol, prepared in preparation 50), to propane-2-sulfonic acid [2-(4-iodo-phenyl)-propyl]-amide (0.20 g, 0.65 mmol, can be prepared as in J. Med. Chem., 43, 4354 (2000)), [1,1′-bis(diphenyl-phosphino)-ferrocene]dichloropalladium(1H) complex with methylene chloride (1:1) (0.013 g, 0.016 mmol), and 2M aqueous sodium carbonate (1.35 mL, 2.7 mmol) in DMF and heat to 80° C. After 3 hours, cool and pour into water. Extract with ethyl acetate. Wash the combined organics with water, and brine, dry over magnesium sulfate, filter and concentrate under reduced pressure. Purify the residue by flash chromatography (silica gel), eluting with ethyl acetate:hexanes to provide the title compound. Mass spectrum (ES+)=446.3 (M+1).

후처리

  1. temperaturecool
  2. extractionExtract with ethyl acetate
  3. washWash the combined organics with water, and brine
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customPurify the residue by flash chromatography (silica gel)
  8. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-b1dd9bd30ea04ab0ae16b769df0e1d14
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07625932B2

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