Isopropyl iodide → Methyl 6-bromo-1-isopropyl-1H-indazole-4-carboxylate

HRID 1909294Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:5]2[CH:6]=[N:7][NH:8][C:9]=2[CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:22]([CH3:24])[CH3:23]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:5]2[CH:6]=[N:7][N:8]([CH:22]([CH3:24])[CH3:23])[C:9]=2[CH:10]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of methyl 6-bromo-1H-indazole-4-carboxylate (4 g, 14.92 mmol) in acetonitrile (30 mL), cesium carbonate (9.7 g, 29.8 mmol) was added followed by 2-iodopropane (3.8 g, 22.3 mmol) and the reaction mixture stirred at 90° C. for 2 h. On completion, the reaction mixture was concentrated under reduced pressure and the residue diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water, brine and dried over sodium sulfate. Solvent was removed under reduced pressure to afford crude material which was purified by column chromatography to afford methyl 6-bromo-1-isopropyl-1H-indazole-4-carboxylate (1.5 g, 32.6%).

Workup

concentrationOn completion, the reaction mixture was concentrated under reduced pressure
additionthe residue diluted with water
extractionextracted with ethyl acetate
washThe combined organic layers were washed with water, brine
dry with materialdried over sodium sulfate
customSolvent was removed under reduced pressure
customto afford crude material which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-f16a71aa397f46b3b333b68201bd0734
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598167B1

Reaction notes

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