Methyl iodide → HCID 67540656, compound

HRID 1192320Notes

Reaction equation

HRID 1192320 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][N:20]=[CH:19]3)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:25]I>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][N:13]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[N:21]([CH3:25])[N:20]=[CH:19]3)[CH2:14][CH2:15]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67538337tert-Butyl 4-(1H-indazol-5-yl)piperazine-1-carboxylate

Product 1

HCID 67540656HCID 67540656, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of NaH (60%, 4 mg, 0.1 mmol) in DMF (0.5 mL) was added dropwise a solution of 4-(1H-Indazol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.100 g, 0.33 mmol) in DMF (1 mL). After stirring for 30 minutes, methyl iodide (0.026 g, 0.18 mmol) was added dropwise. The mixture was stirred at room temperature for 2 hours and then partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (hexanes:EtOAc, 2:1) to give 4-(1-Methyl-1H-indazol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.023 g, 22%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.87 (s, 1H), 7.32 (d, J=9.2 Hz, 1H), 7.20 (d, J=9.2 Hz, 1H), 7.12 (s, 1H), 4.04 (s, 3H), 3.62 (m, 4H), 3.09 (m, 4H), 1.50 (s, 9H). LCMS (APCI+) m/z 317 [M+H]+; Rt=3.31 minutes.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. custompartitioned between EtOAc and water
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (hexanes:EtOAc, 2:1)

Sources & evidence

ORD record
ord-be6a3d7eece24fd7aca1d176d8f436bb
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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