Sodium bis(trimethylsilyl)amide → HCID 123585157, compound

HRID 2209258Notes

Reaction equation

HRID 2209258 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C.C1COCC1>[Br:1][C:2]1[C:7]([O:8][CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 147400532-Bromo-5-chloropyridin-3-ol

Product 1

HCID 123585157HCID 123585157, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of 2-bromo-5-chloropyridin-3-ol (2.6 g) in DMF (50 mL) was added a 1 M solution of NaHMDS in THF (15 mL), after 30 min., (2-(chloromethoxy)ethyl)trimethylsilane (2.496 g) was added. After stifling for 2 hours at rt., The reaction mixture was extracted with ethyl acetate and washed with brine. After drying and removing the solvent, the residue was purified by silica gel chromatography to provide 3.9 g of 2-bromo-5-chloro-3-((2-(trimethylsilyl)ethoxy)methoxy)pyridine. LCMS [M+H]+: 339.8. 1HNMR (400 MHz, CDCl3) ppm: δ 8.01 (d, J=2.2 Hz, 1H), 7.45 (d, J=2.2 Hz, 1H), 5.31 (s, 2H), 3.79 (t, J=8.4 Hz, 2H), 0.92 (t, J=8.4 Hz, 2H), 0.08 (s, 9H).

Workup

  1. waitAfter stifling for 2 hours at rt
  2. extraction, The reaction mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. customAfter drying
  5. customremoving the solvent
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d18cd18ece77475a8478cd68e35043dc
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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