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Hydrochloric Acid → (Z)-4-azido-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one

HRID 324961
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HRID 324961 반응식
F[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:15]/[C:16]1[NH:17][CH:18]=[CH:19][C:20]=1[O:21][CH3:22])/[C:5](=[O:14])[NH:6]2.C(N(C(C)C)CC)(C)C.C[Si]([N:36]=[N+:37]=[N-:38])(C)C.Cl>C1COCC1.C(O)C>[N:36]([C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:15]/[C:16]1[NH:17][CH:18]=[CH:19][C:20]=1[O:21][CH3:22])/[C:5](=[O:14])[NH:6]2)=[N+:37]=[N-:38]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 78378AzidotrimethylsilaneHCID 81531DiisopropylethylamineHCID 15512601(Z)-1,3-Dihydro4-fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one2회

생성물 1

HCID 15512602(Z)-4-azido-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 8028Tetrahydrofuran용매

실험 절차

(Z)-1,3-Dihydro4-fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one (6.60 g, 21.8 mmol) (Starting Material 3 above) was suspended in 330 mL of THF and 165 mL of ethanol. To this mixture was added diisopropylethylamine (56.9 ml, 326 mmol) (Aldrich) and trimethylsilyl azide (28.6 mL, 218 mmol) (Aldrich). The reaction mixture was heated at reflux overnight, and then poured into 2 L mixture of ice and 1 N HCl solution. The solid precipitate was filtered, washed with water and dried at 50° C. under high vacuum to give (Z)4-azido-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one as a dark red solid. (Yield 6.44 g, 90%)

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe solid precipitate was filtered
  4. washwashed with water
  5. customdried at 50° C. under high vacuum

출처 및 근거

ORD 기록
ord-d1d8a156fd55474bbc1d18874cfc8f4e
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06221867B1

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