Methyl iodide → Methyl 6-bromo-1-methyl-1H-indazole-3-carboxylate

HRID 1689785Notes

Reaction equation

HRID 1689785 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:14])=[O:12])=[N:7][NH:8]2)=[CH:4][CH:3]=1.[C:15](=O)([O-])[O-].[K+].[K+].CI>C(#N)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:14])=[O:12])=[N:7][N:8]2[CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 46784006Methyl 6-bromo-1H-indazole-3-carboxylate

Product 1

HCID 46942338Methyl 6-bromo-1-methyl-1H-indazole-3-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of methyl 6-bromo-1H-indazole-3-carboxylate (0.50 g, 1.96 mmol) and potassium carbonate (1.28 g, 9.29 mmol) in acetonitrile (15 mL) is added methyl iodide (1.31 g, 9.29 mmol) at room temperature. The reaction mixture is stirred at room temperature for 15 h. Remove the solvent under vacuum, dilute with water, and extract with ethyl acetate (3×10 mL). The combined organics are dried over sodium sulfate and concentrated under reduced pressure. The crude is purified by flash chromatography eluting with 8:2 hexane/ethyl acetate to give 0.35 g (70%) of the title compound as an off white solid. 1H NMR (400 MHz, CDCl3) δ 4.03 (s, 3H), 4.14 (s, 3H), 7.42 (dd, J=8.4, 1.2 Hz, 1H), 7.66 (s, 1H), 8.08 (d, J=8.8 Hz, 1H).

Workup

  1. customRemove the solvent under vacuum
  2. additiondilute with water
  3. extractionextract with ethyl acetate (3×10 mL)
  4. dry with materialThe combined organics are dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude is purified by flash chromatography
  7. washeluting with 8:2 hexane/ethyl acetate

Sources & evidence

ORD record
ord-b966b5743a9545c29c40b4b9afc75f2f
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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