Diisopropylethylamine → Ethyl 3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-4-carboxylate

HRID 42272Notes

Reaction equation

HRID 42272 reaction equation
[I:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[CH3:21][Si:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25][CH2:26]Cl>ClCCl.[Cl-].[Na+].O>[I:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])[N:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178469927HCID 178469927, compound

Product 1

HCID 67505121Ethyl 3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of EXAMPLE 59A (1.3 g, 5 mmole) and diisopropyl-ethyl amine (1.3 mL, 7.5 mmole) in dichloromethane (20 mL) at ambient temperature was added 2-(trimethylsilyl)ethoxymethyl chloride (1.25 g, 7.5 mmole) dropwise. The solution was stirred overnight. Brine (20 mL) was added and the mixture was extracted with ethyl acetate. The mixture was dried with magnesium sulfate, filtered and concentrated. The residue was purified on a silica gel column eluting with 25% ethyl acetate in hexane. The two regioisomers were isolated as a mixture. MS (DCI) m/e 397 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe mixture was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel column
  6. washeluting with 25% ethyl acetate in hexane
  7. customThe two regioisomers were isolated as a mixture

Sources & evidence

ORD record
ord-34c59c89e1c0457e990b2b04352e16d5
Source dataset
uspto-grants-2013_09
Patent number
US08536180B2

Reaction notes

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