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

HRID 624036Notes

Reaction equation

HRID 624036 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-30162e6852b94abea4ea7e2149d539a8
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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