Pyrrolidine → HCID 178517057, compound

HRID 1615268Notes

Reaction equation

HRID 1615268 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[N:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:25]=[C:24]([CH:26]=O)[CH:23]=[C:22]3[C:18]=2[CH:19]=[N:20][N:21]3COCC[Si](C)(C)C)=[CH:13][CH:12]=1.N1CCCC1>C(O)C>[N:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:25]=[C:24]([CH:26]=[C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][C:2]3=[O:10])[CH:23]=[C:22]3[C:18]=2[CH:19]=[N:20][NH:21]3)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 321710OxindoleHCID 86651954HCID 86651954, compound

Product 1

HCID 178517057HCID 178517057, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of oxindole (12 mg, 0.08 mmol) and 4-(pyridin-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (31 mg, 0.087 mmol) in ethanol (2 mL) was added pyrrolidine (20 μL). The mixture was heated to 70° C. for 3 h. The solution was concentrated to dryness and treated with 4M HCl (1 mL) in ethanol (3 mL) at 70° C. for 4 h. The solution was cooled to rt and extracted with ethyl acetate (50 mL), dried over MgSO4 and concentrated to give the title compound as a mixture of E/Z isomers which were separated by preparatory HPLC.

Workup

  1. concentrationThe solution was concentrated to dryness
  2. additiontreated with 4M HCl (1 mL) in ethanol (3 mL) at 70° C. for 4 h
  3. temperatureThe solution was cooled to rt
  4. extractionextracted with ethyl acetate (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4e413dd7b92f46b3ad2a3f7ad77977ca
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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