Sodium hydride → HCID 59191584, compound

HRID 1479978Notes

Reaction equation

HRID 1479978 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:14][Si:15]([CH2:18][CH2:19][O:20][CH2:21]Cl)([CH3:17])[CH3:16]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:9])([O:11][CH2:21][O:20][CH2:19][CH2:18][Si:15]([CH3:17])([CH3:16])[CH3:14])[CH3:10])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 223919732-(6-Bromo-3-pyridyl)-2-propanol

Product 1

HCID 59191584HCID 59191584, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To compound 31 (532 mg, 2.46 mmol) in anhydrous DMF (5 mL) at 0° C. is added sodium hydride (60% in mineral oil, 138 mg, 3.45 mmol). The mixture is stirred at rt for 1 h and then cooled to 0° C., to which is added SEMCl (0.564 uL, 3.2 mmol). The mixture is stirred at rt for 16 h, 50° C. for 1 h, cooled to rt and quenched with water, extracted with ethyl acetate. The organic phase is washed with brine, dried and rotavaped. The oily residue is purified by silica gel chromatography (10-15% ethyl acetate in heptane) to afford the title compound as clear oil (474 mg, 56%).

Workup

  1. temperaturecooled to 0° C., to which
  2. stirringThe mixture is stirred at rt for 16 h, 50° C. for 1 h
  3. temperaturecooled to rt
  4. customquenched with water
  5. extractionextracted with ethyl acetate
  6. washThe organic phase is washed with brine
  7. customdried
  8. customThe oily residue is purified by silica gel chromatography (10-15% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-66502bb0d852441daca04c4bb51428df
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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