Pyridine → 1-(3-methyl-1H-indazol-1-yl)Ethanone

HRID 2224673Notes

Reaction equation

HRID 2224673 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.N1C=CC=CC=1.[CH3:17][C:18](OC(C)=O)=[O:19]>C1COCC1.CN(C1C=CN=CC=1)C>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:18](=[O:19])[CH3:17])[N:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178434273HCID 178434273, compound

Product 1

HCID 126391861-(3-methyl-1H-indazol-1-yl)EthanoneYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-Methylindazole (1.00 g, 7.6 mmol) was dissolved in 10 ml THF and stirred at RT under a blanket of argon. Pyridine (0.64 ml, 7.9 mmol) was added followed by Ac2O (0.79 ml, 8.3 mmol) and catalytic DMAP (90 mg, 0.7 mmol). The reaction proceeded for 2 h and was then partitioned between 1N HCl and dichloromethane. The organic phase was dried over MgSO4 and concentrated in vacuo to a tan solid (1.2 g, 91% yield).

Workup

  1. customwas then partitioned between 1N HCl and dichloromethane
  2. dry with materialThe organic phase was dried over MgSO4

Sources & evidence

ORD record
ord-16d7e8e76d554946a5127986b0e59a31
Source dataset
uspto-grants-2008_05
Patent number
US07378441B2

Reaction notes

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