Methyl iodide → Benzyl 3-methyl-2-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,2',3,3'-tetrahydro-1H,1'H-spiro[1,8-naphthyridine-4,4'-pyridine]-1'-carboxylate

HRID 1664802Notes

Reaction equation

HRID 1664802 reaction equation
[O:1]=[C:2]1[CH2:26][C:10]2([CH:15]=[CH:14][N:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH2:12][CH2:11]2)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32].I[CH3:36]>O1CCCC1>[CH3:36][CH:26]1[C:10]2([CH:11]=[CH:12][N:13]([C:16]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:17])[CH2:14][CH2:15]2)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:2]1=[O:1]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 57663850benzyl 2-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,2',3,3'-tetrahydro-1H,1'H-spiro[1,8-naphthyridine-4,4'-pyridine]-1'-carboxylate

Product 1

HCID 67440829Benzyl 3-methyl-2-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,2',3,3'-tetrahydro-1H,1'H-spiro[1,8-naphthyridine-4,4'-pyridine]-1'-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hexamethyldisilylazide (1.0 M in THF; 0.135 mL, 0.135 mmol) was added to solution of benzyl 2-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,2′,3,3′-tetrahydro-1H,1′H-spiro[1,8-naphthyridine-4,4′-pyridine]-1′-carboxylate (50.0 mg, 0.104 mmol) in tetrahydrofuran (1 mL) at −78° C. After 40 min, iodomethane (8.0 μL, 0.135 mmol) was added and the reaction mixture was slowly warmed to ambient temperature. After 1 h, the mixture was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate (3×). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated to give the title compound. MS 494.3 (M+1).

Workup

  1. waitAfter 1 h
  2. customthe mixture was quenched with saturated aqueous ammonium chloride
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a3eaa2a469ba43bd94adf6c8094550e6
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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