5,6-Dimethoxyindoline → 5,6-dimethoxy-1-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)indoline

HRID 624017Notes

Reaction equation

HRID 624017 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].[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[NH:19][CH2:18][CH2:17]2>C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]([CH2:10][CH2:9][N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[N:6]1)[CH2:18][CH2:17]2

Participants

4

Reactant 2

HCID 110629785,6-DimethoxyindolineHCID 25220516(4-nitro-1H-pyrazol-1-yl)acetaldehyde

Product 1

HCID 682834525,6-dimethoxy-1-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)indoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-nitro-1H-pyrazol-1-yl)acetaldehyde (942 mg, 6.08 mmol) in DCM (60.0 mL), 5,6-dimethoxyindoline (from step 1) (1.09 g, 6.08 mmol) and STAB (1.55 g, 7.29 mmol) was added. 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/hex 1:4 to 1:1) to yield 5,6-dimethoxy-1-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)indoline as a brown solid. LC-MS conditions B: tR=0.65 min, [M+H]+=319.19.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with DCM (2×)
  3. concentrationlayers were concentrated
  4. custompurification

Sources & evidence

ORD record
ord-5c6c99cad5264a77b733aa7509b4e614
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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