Dicyclohexylcarbodiimide → t-Butyl 5-{[5-(2-pyridyldithiomethyl)benzofuran-2-ylcarbonyl]amino}indole-2-carboxylate

HRID 2259845노트

반응식

HRID 2259845 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([C:18]([OH:20])=O)=[CH:15][C:14]=2[CH:21]=1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:37][C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][C:42]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[CH:41]2>C1COCC1.C(Cl)Cl.CN(C)C1C=CN=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([C:18]([NH:37][C:38]3[CH:39]=[C:40]4[C:44](=[CH:45][CH:46]=3)[NH:43][C:42]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[CH:41]4)=[O:20])=[CH:15][C:14]=2[CH:21]=1

참가 물질

7

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 10633339Tert-butyl 5-amino-1H-indole-2-carboxylateHCID 153454855-(2-Pyridyldithiomethyl)benzofuran-2-carboxylic acid

생성물 1

HCID 15345486t-Butyl 5-{[5-(2-pyridyldithiomethyl)benzofuran-2-ylcarbonyl]amino}indole-2-carboxylate

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매3회HCID 8028Tetrahydrofuran용매

실험 절차

A stirred solution of 15 (247 mg, 0.78 mmol) in 30 mL dry THF at room temperature under argon, was treated sequentially with solutions of dicyclohexylcarbodiimide (177 mg, 0.86 mmol) in 5 mL methylene chloride, 4-(dimethylamino)pyridine (29 mg, 0.23 mmol) in 2 mL methylene chloride, and 10 (200 mg, 0.86 mmol) in 5 mL methylene chloride. The reaction mixture was stirred overnight. Dicyclohexylurea was filtered from the reaction mixture, and the filtrate was washed with water, cold 0.1M HCl, saturated aqueous sodium bicarbonate, and water. The organic solution was dried over magnesium sulfate, filtered, and concentrated to give a dark oil. The crude product was further purified by chromatography on a silica gel column, eluting with ethyl acetate:hexanes to give 16 as an off-white solid: NMR (acetone-d6) δ 1.6 (s, 9H), δ 4.3 (s, 2H), δ 7.0-8.6 (m, 12H).

후처리

  1. filtrationDicyclohexylurea was filtered from the reaction mixture
  2. washthe filtrate was washed with water, cold 0.1M HCl, saturated aqueous sodium bicarbonate, and water
  3. dry with materialThe organic solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a dark oil
  7. customThe crude product was further purified by chromatography on a silica gel column
  8. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-1a9d81e659c84128a86f8f2a65390cfd
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05475092

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