Methyl iodide → HCID 57545953, compound

HRID 913825Notes

Reaction equation

HRID 913825 reaction equation
[C:1]1([C:7]2([CH2:20][O:21][CH2:22][C:23]3[C:31]4[C:27](=[CH:28][N:29]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[N:30]=4)[CH:26]=[C:25]([C:40]([F:43])([F:42])[F:41])[CH:24]=3)[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:44]([Li])(C)(C)C.IC.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH3:44][C:28]1[N:29]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:37])([CH3:39])[CH3:38])[N:30]=[C:31]2[C:27]=1[CH:26]=[C:25]([C:40]([F:41])([F:43])[F:42])[CH:24]=[C:23]2[CH2:22][O:21][CH2:20][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH2:11][CH2:12]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 86626241HCID 86626241, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 57545953HCID 57545953, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-phenyl-4-(((5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methoxy)methyl)piperidine-1-carboxylate (97 mg, 0.16 mmol) was dissolved in dry tetrahydrofuran (3 mL) and stirred at room temperature for 15 min. The stirred mixture was cooled to −78° C. and treated with a solution of tert-butyllithium (1.7 M in pentane, 190 μL, 0.33 mmol). The reaction was gradually warmed to −20° C. over 1 h, cooled to −78° C. and treated with iodomethane (10 μL, 0.19 mmol). The reaction was warmed to 0° C. over several hours then treated with saturated ammonium chloride. The reaction was diluted with ethyl acetate. The layers were separated and the organic layer washed with brine (2×), dried over sodium sulfate, filtered and concentrated to afford 100 mg (quant.) as a clear oil. LC/MS (HPLC method 1): tR=3.70 min, 634.26(MH)+.

Workup

  1. temperatureThe stirred mixture was cooled to −78° C.
  2. temperatureThe reaction was gradually warmed to −20° C. over 1 h
  3. temperaturecooled to −78° C.
  4. temperatureThe reaction was warmed to 0° C. over several hours
  5. customThe layers were separated
  6. washthe organic layer washed with brine (2×)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford 100 mg (quant.) as a clear oil

Sources & evidence

ORD record
ord-abfb7052768f4d3196f0b16f3b877674
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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