Methyl iodide → HCID 59233018, compound

HRID 1925161Notes

Reaction equation

HRID 1925161 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH3:15][Si](C)(C)[N-][Si](C)(C)C.[Li+].IC>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 59233032HCID 59233032, compound

Product 1

HCID 59233018HCID 59233018, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(6-chloropyridazin-3-yl)propanoate (2.8 g, 13.04 mmol) in THF (28 mL) was added lithium hexamethyldisilazide (1.0 molar in THF, 15.65 mL, 15.65 mmol) at −70° C. in dropwise fashion. The reaction was stirred at −70 for 30 min and then iodomethane (0.816 mL, 13.04 mmol) was added. The reaction was stirred for 2 hrs as allowed to warm to room temperature. The reaction was concentrated to dryness via rotary evaporation and the resulting material was purified by MPLC (98:2, DCM:MeOH) to provide the title compound, ethyl 2-(6-chloropyridazin-3-yl)-2-methylpropanoate (54B, 2.82 g, 95%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.11 (t, J=7.07 Hz, 3 H) 1.58 (s, 6 H) 4.08 (q, J=7.07 Hz, 2 H) 7.83-7.97 (m, 2 H).

Workup

  1. stirringThe reaction was stirred for 2 hrs
  2. concentrationThe reaction was concentrated to dryness via rotary evaporation
  3. customthe resulting material was purified by MPLC (98:2, DCM:MeOH)

Sources & evidence

ORD record
ord-a4730bc6b72f47ff9769a9f173c8312d
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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