Tributylvinyltin → 3-Ethenyl-1-methyl-1h-indazole

HRID 530813Notes

Reaction equation

HRID 530813 reaction equation
C(=O)(O)N.[N:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14](OC)=O)[CH:6]=1.[CH:18]([Sn](CCCC)(CCCC)CCCC)=[CH2:19]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:10][N:9]1[C:8]2[C:7](=[CH:14][CH:11]=[CH:12][CH:13]=2)[C:6]([CH:18]=[CH2:19])=[N:5]1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 90419258Methyl pyrazolo[1,5-a]pyridine-3-carboxylate carbamate

Product 1

HCID 206447223-Ethenyl-1-methyl-1h-indazole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of compound 1 (1.6 g, 8 mmol) and vinyl tributyl tin (2.6 mL, 11 mmol) in toluene (10 mL) was treated with Pd(PPh3)4 (0.92 g, 0.8 mmol) and heated to reflux overnight. The reaction mixture was concentrated and the resulting material was purified directly by gradient elution on silica gel (0 to 20% EtOAc in hexanes) to afford the title compound as a colorless oil.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationThe reaction mixture was concentrated
  4. customthe resulting material was purified directly by gradient elution on silica gel (0 to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2844ee1d85bd434aa3469eb345bfd485
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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