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

HRID 1854112Notes

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-9ff0fff8dded40debb9afc73f23f609b
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962620B2

Reaction notes

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