Tetrahydrofuran → 1-(2-Benzyl-3-phenyl-2h-indazol-7-yl)ethanone

HRID 735468Notes

Reaction equation

HRID 735468 reaction equation
[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:15]2[C:10](C(C(O)=O)=CC=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li][CH3:27].[CH2:28]1[CH2:32][O:31][CH2:30][CH2:29]1>>[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:28]([C:32](=[O:31])[CH3:27])=[CH:29][CH:30]=[CH:14]2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 67021115HCID 67021115, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 670210041-(2-Benzyl-3-phenyl-2h-indazol-7-yl)ethanone

Procedure

2-Benzyl-3-phenyl-2H-indazole-7-carboxylic acid (0.5 mmol, 160 mg, see preparation of Example 518) was dissolved in 5 ml of dry THF at 0° C. Two milliliters (2 ml) of MeLi (1.6M solution in THF) were added dropwise and the mixture was stirred overnight at room temperature. The reaction mixture was quenched with aq NH4Cl solution and the product was extracted with EtOAc, and then flash column chromatography (SiO2, dichloromethane as an eluant) afforded 1-(2-benzyl-3-phenyl-2H-indazol-7-yl)ethanone in 61% yleld.

Workup

  1. customThe reaction mixture was quenched with aq NH4Cl solution
  2. extractionthe product was extracted with EtOAc

Sources & evidence

ORD record
ord-3285cf337324464392ab5406dba0c327
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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