Diisopropylethylamine → 5-Bromo-2-(2-{[2-(trimethylsilyl)ethoxy]methoxy}propan-2-yl)pyridine

HRID 351743Notes

Reaction equation

HRID 351743 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[N:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[CH3:21][Si:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25][CH2:26]Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:9])([O:11][CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])[CH3:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 154863922-(5-Bromopyridin-2-yl)propan-2-ol

Product 1

HCID 108609105-Bromo-2-(2-{[2-(trimethylsilyl)ethoxy]methoxy}propan-2-yl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-(1-hydroxy-1-methylethyl)pyridine from Step 1 (14 mmol) in methylene chloride (50 mL) at 0° C. was added N,N-diisopropylethylamine (37.3 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (15.3 mmol). The resulting mixture was stirred at room temperature for 18 hours, then refluxed for 24 hours. After cooling to room temperature the mixture was quenched with saturated aqueous ammonium chloride solution and partitioned between methylene chloride and water. The crude product from the organic phase was chromatographed on silica gel eluting with 6% ethyl acetate in hexane to afford the 5-bromo-2-(1-methyl-1-{[2-(trimethylsilyl)ethoxy]methoxy}ethyl)pyridine compound.

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureAfter cooling to room temperature the mixture
  3. customwas quenched with saturated aqueous ammonium chloride solution
  4. custompartitioned between methylene chloride and water
  5. customThe crude product from the organic phase was chromatographed on silica gel eluting with 6% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6358340ec48e43a3ba2ef2a6fb343f54
Source dataset
uspto-grants-2004_06
Patent number
US06743802B2

Reaction notes

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