Methyl iodide → HCID 68314590, compound

HRID 1618104Notes

Reaction equation

HRID 1618104 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:24])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH:12]1[CH2:17][CH2:16][N:15]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]1)[CH2:7]2.CI.[CH3:27][Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([F:24])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH:12]1[CH2:13][CH2:14][N:15]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:16][CH2:17]1)[CH:7]2[CH3:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 67194237HCID 67194237, compound

Product 1

HCID 68314590HCID 68314590, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 7-bromo-2-(1-cyclohexylpiperidin-4-yl)-5-fluoro-2,3-dihydro-1H-isoindol-1-one (70 mg, 0.177 mmol) and methyliodide (1.1 equiv., 0.195 mmol, 0.012 mL) in anhydrous tetrahydrofuran (3.5 mL) under nitrogen at −78° C., 1M sodium bis(trimethylsilyl)amide in tetrahydrofuran (1.2 equiv., 0.212 mL) was slowly added. The reaction mixture was stirred for 90 min and quenched by adding dropwise a 10% ammonium hydroxide solution. Dichloromethane was added, the layers were separated, and the aqueous layer was extracted twice dichloromethane. Organic layers were collected, dried and evaporated. Crude (58 mg) was used without further purification.

Workup

  1. customquenched
  2. additionby adding dropwise a 10% ammonium hydroxide solution
  3. additionDichloromethane was added
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted twice dichloromethane
  6. customOrganic layers were collected
  7. customdried
  8. customevaporated
  9. customCrude (58 mg) was used without further purification

Sources & evidence

ORD record
ord-179b5fa91aac4518be1e93519329ff85
Source dataset
uspto-grants-2014_07
Patent number
US08765972B2

Reaction notes

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