Water → 1-(3-(4-nitro-1H-pyrazol-1-yl)propyl)indoline

HRID 624022노트

반응식

HRID 624022 반응식
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][CH:11]=O)[CH:8]=1)([O-:3])=[O:2].[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.O>CC#N.C(Cl)Cl.CC(O)=O>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][CH2:11][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[CH:8]=1)([O-:3])=[O:2]

참가 물질

7

반응물 3

HCID 962WaterHCID 10328IndolineHCID 630411263-(4-nitro-1H-pyrazol-1-yl)propanal

생성물 1

HCID 867042081-(3-(4-nitro-1H-pyrazol-1-yl)propyl)indoline

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 3-(4-nitro-1H-pyrazol-1-yl)propanal (722 mg, 4.27 mmol) in MeCN (7.0 mL) and DCM (5.0 mL), indoline (0.48 mL, 4.27 mmol) was added, followed by STAB (1.36 g, 6.40 mmol) and one drop of AcOH. The resulting yellow suspension was stirred at rt for 1 h 15 min, then water and DCM was added and the org. layer was separated. The aq. layer was extracted with DCM and the combined org. layers were washed with brine, dried (MgSO4), filtered and the solvent was removed under reduced pressure to yield 1-(3-(4-nitro-1H-pyrazol-1-yl)propyl)indoline as a yellow oil which was used without further purification in the next step. LC-MS conditions B: tR=0.76 min, [M+H]+=273.06.

후처리

  1. customlayer was separated
  2. extractionThe aq. layer was extracted with DCM
  3. washlayers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-05e355aab7d343b1ad51cd299d819323
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303023B2

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