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

HRID 624022ノート

反応式

HRID 624022 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-05e355aab7d343b1ad51cd299d819323
出典データセット
uspto-grants-2016_04
特許番号
US09303023B2

反応ノート

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