Sodium hydride → HCID 67286765, compound

HRID 2390809Notes

Reaction equation

HRID 2390809 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:46]([C:47]2[CH:48]=[C:49]([C:57]([CH3:60])([CH3:59])[CH3:58])[C:50]([O:55][CH3:56])=[C:51]([CH:54]=2)[CH:52]=O)=[CH:45][CH:44]=[C:43]([CH3:61])[N:42]=1)[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:46]([C:47]2[CH:54]=[C:51]([CH:52]=[CH:9][C:8]3[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:30][CH:29]=3)[C:50]([O:55][CH3:56])=[C:49]([C:57]([CH3:59])([CH3:58])[CH3:60])[CH:48]=2)=[CH:45][CH:44]=[C:43]([CH3:61])[N:42]=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 86638341HCID 86638341, compound

Product 1

HCID 67286765HCID 67286765, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

step 4—To a solution of 4-nitro-benzyltriphenylphosphonium bromide (829 mg, 1.734 mmol) in DMF (5 mL) at 0° C. was added NaH (60% in oil dispersion, 133 mg, 3.32 mmol). The reaction was stirred for 30 min at 0° C. and followed by addition of a solution of 66 (215 mg, 0.553 mmol) in DMF (5 mL). The resulting mixture was gradually warmed to RT and stirred overnight. The reaction was quenched with 1N aqueous HCl solution (6 mL) then 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 (0 to 4% EtOAc) to afford 180 mg (64%) of 2-benzyloxy-3-{3-tert-butyl-4-methoxy-5-[2-(4-nitro-phenyl)-vinyl]-phenyl}-6-methyl-pyridine (68) as an orange 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. additionthen diluted 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 (0 to 4% EtOAc)

Sources & evidence

ORD record
ord-012d543103034725b7d522cb8badc812
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

Loading…