Sodium hydride → HCID 67069886, compound

HRID 2390805Notes

Reaction equation

HRID 2390805 reaction equation
[Br-].[N+:2]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:7][CH:6]=1)([O-:4])=[O:3].[H-].[Na+].[CH2:33]([O:40][C:41]1[C:48]([C:49]2[C:50]([O:55][CH3:56])=[N:51][CH:52]=[CH:53][CH:54]=2)=[CH:47][C:46]([C:57]([CH3:60])([CH3:59])[CH3:58])=[CH:45][C:42]=1[CH:43]=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C>[CH2:33]([O:40][C:41]1[C:42]([CH:43]=[CH:9][C:8]2[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:30][CH:29]=2)=[CH:45][C:46]([C:57]([CH3:60])([CH3:59])[CH3:58])=[CH:47][C:48]=1[C:49]1[C:50]([O:55][CH3:56])=[N:51][CH:52]=[CH:53][CH:54]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 197008[(4-Nitrophenyl)methyl](triphenyl)phosphanium bromideHCID 86638340HCID 86638340, compound

Product 1

HCID 67069886HCID 67069886, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

step 3—To a solution of 4-nitro-benzyltriphenylphosphonium bromide (1.07 g, 2.238 mmol) in DMF (8 mL) at 0° C., was added NaH (60% in oil dispersion, 156 mg, 3.90 mmol). The reaction was stirred for 30 min at 0° C. then a solution of 50 (281 mg, 0.749 mmol) in DMF (6 mL) was added. The resulting mixture was gradually warmed to RT and stirred overnight. The reaction was quenched with 1N aqueous HCl solution (6 mL) and diluted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (5 to 10% EtOAc) to afford 311 mg (84%) of 3-{2-benzyloxy-5-tert-butyl-3-[2-(4-nitro-phenyl)-vinyl]-phenyl}-2-methoxy-pyridine (52) as a yellow oil.

Workup

  1. temperatureThe resulting mixture was gradually warmed to RT
  2. stirringstirred overnight
  3. customThe reaction was quenched with 1N aqueous HCl solution (6 mL)
  4. additiondiluted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified by SiO2 chromatography
  10. washeluting with an EtOAc/hexane gradient (5 to 10% EtOAc)

Sources & evidence

ORD record
ord-7dbcd044cf7b44169001bc18924c8e1a
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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