Ethylenediamine → 5-cyclopropyl-1H-indazole

HRID 246197노트

반응식

HRID 246197 반응식
[CH:1]1([C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[N:9](COCC[Si](C)(C)C)[N:8]=[CH:7]3)[CH2:3][CH2:2]1.C(N)CN>ClCCl.FC(F)(F)C(O)=O>[CH:1]1([C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[NH:9][N:8]=[CH:7]3)[CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 3301EthylenediamineHCID 712800795-cyclopropyl-1-(2-trimethylsilanylethoxymethyl)-1H-indazole

생성물 1

HCID 692087495-cyclopropyl-1H-indazole수율 107.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

In a 1 L round-bottomed flask, 5-cyclopropyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (1.7 g, 5.89 mmol) was dissolved in a solution of dichloromethane (292 mL) and trifluoroacetic acid (194 mL). After stirring at room temperature overnight, the reaction mixture was concentrated under reduced pressure. The resultant crude solid was dissolved in dichloromethane and ethylenediamine (24.2 mL, 5.89 mmol) was added. After stirring at room temperature overnight, the reaction mixture was poured onto water (50 mL) and extracted with EtOAc (2×100 mL). The organic layers were dried over MgSO4 and concentrated under reduced pressure to afford 1 g of 5-cyclopropyl-1H-indazole that was used without further purification.

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe resultant crude solid was dissolved in dichloromethane
  3. stirringAfter stirring at room temperature overnight
  4. additionthe reaction mixture was poured onto water (50 mL)
  5. extractionextracted with EtOAc (2×100 mL)
  6. dry with materialThe organic layers were dried over MgSO4
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5ea19a24b073438fa3a1da5bc3415e1b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

반응 노트

불러오는 중…