Indoline → 1-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)indoline

HRID 624036노트

반응식

HRID 624036 반응식
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH:10]=O)[CH:8]=1)([O-:3])=[O:2].[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1>CC#N>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH:8]=1)([O-:3])=[O:2]

참가 물질

4

반응물 2

HCID 10328IndolineHCID 25220516(4-nitro-1H-pyrazol-1-yl)acetaldehyde

생성물 1

HCID 682835761-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)indoline

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

To a solution of 2-(4-nitro-1H-pyrazol-1-yl)acetaldehyde (1.02 g, 4.97 mmol) in MeCN (18.0 mL), indoline (0.56 mL, 4.95 mmol) dissolved in MeCN (6 mL) was added. The resulting orange solution was stirred at rt for 5 min, then STAB (2.10 g, 9.90 mmol) was added in portions. After stirring at rt for 1 h, the reaction mixture was quenched with water and extracted with DCM (2×). The combined org. layers were concentrated and purification was performed by FC (EtOAc/toluene 2:8) to yield 1-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)indoline as a brown solid. LC-MS conditions A: tR=0.85 min, [M+H]+=259.14.

후처리

  1. additionwas added
  2. additionSTAB (2.10 g, 9.90 mmol) was added in portions
  3. stirringAfter stirring at rt for 1 h
  4. customthe reaction mixture was quenched with water
  5. extractionextracted with DCM (2×)
  6. concentrationlayers were concentrated
  7. custompurification

출처 및 근거

ORD 기록
ord-30162e6852b94abea4ea7e2149d539a8
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303023B2

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