N-methyl-2-pyrrolidone → 1-(2-butylsulfanyl-pyrimidin-4-yl)-4-nitro-1H-indazole

HRID 1946992노트

반응식

HRID 1946992 반응식
[CH2:1]([S:5][C:6]1[N:11]=[C:10](Cl)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].[N+:13]([C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH:18]=[N:19][NH:20]2)([O-:15])=[O:14].[H-].[Na+].CN1C(=O)CCC1>O>[CH2:1]([S:5][C:6]1[N:11]=[C:10]([N:20]2[C:21]3[C:17](=[C:16]([N+:13]([O-:15])=[O:14])[CH:24]=[CH:23][CH:22]=3)[CH:18]=[N:19]2)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 4

HCID 13387N-methyl-2-pyrrolidoneHCID 180574-NitroindazoleHCID 24758Sodium hydrideHCID 597434972-Butylsulfanyl-4-chloro-pyrimidine

생성물 1

HCID 597435151-(2-butylsulfanyl-pyrimidin-4-yl)-4-nitro-1H-indazole수율 47.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a flask loaded with 2-butylsulfanyl-4-chloro-pyrimidine (202 mg) was added 4-nitro-1H-indazole (228 mg), followed by NaH (60% dispersion in mineral oil, 84 mg) and NMP (4 mL). The resulting mixture was stirred at RT overnight, water added, and the mixture extracted with EtOAc. The combined organic extracts were washed with water, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 80:20) to give 1-(2-butylsulfanyl-pyrimidin-4-yl)-4-nitro-1H-indazole (156 mg).

후처리

  1. extractionthe mixture extracted with EtOAc
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 80:20)

출처 및 근거

ORD 기록
ord-028e3271d016484f8c8668886a636f49
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399462B2

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