Reaction #965698

Reaction equation

N-methoxy-N-methylacetamide

6-bromo-1H-indazole

n-BuLi

→

title compound 24-a

Yield 9.1%

1-(1H-indazol-6-yl)ethanone

Yield 9.1%

Solvents

THF

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction mixture was stirred for another 2 h at −65° C.
2. 2
   Otherquenched with 40 mL H2O
3. 3
   ExtractionThe mixture was extracted with EtOAc (3×50 mL)
4. 4
   WashThe combined organic layers were washed with 100 mL brine
5. 5
   Otherdried
6. 6
   Concentrationconcentrated to dryness
7. 7
   OtherThe residue was purified by flash column chromatography (PE/EA=40/1)

Procedure

To a solution of 6-bromo-1H-indazole (5.0 g, 25.4 mmol) in 40 mL THF was added dropwise n-BuLi (2.5M, 30 mL, 76.2 mmol) at −65° C., and the mixture was stirred for 2 h. Then, N-methoxy-N-methylacetamide (2.9 g, 27.9 mmol) was added. The reaction mixture was stirred for another 2 h at −65° C., then quenched with 40 mL H2O. The mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with 100 mL brine, dried, and concentrated to dryness. The residue was purified by flash column chromatography (PE/EA=40/1) to give the title compound 24-a (370 mg, 9%) as a yellow solid. [M+H] Calc'd for C9H8N2O, 161; Found, 161.

Source