Sodium hydride → HCID 71135258, compound

HRID 1468822Notes

Reaction equation

HRID 1468822 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][OH:18])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29][CH3:30])=[CH:25][CH:24]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][O:18][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([S:29][CH3:30])=[CH:25][CH:24]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 113679304-(Methylthio)benzyl bromideHCID 71136663HCID 71136663, compound

Product 1

HCID 71135258HCID 71135258, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of step B (1.5 g, 4.8 mmol) was dissolved in DMF (15 mL), and sodium hydride (60 wt % dispersion in oil, 290 mg, 7.3 mmol) was added. After stirring at RT for 1 hour, (4-(bromomethyl)phenyl)(methyl)sulfane (1.35 g, 6.2 mmol) was added, and the resulting solution was stirred at RT for 18 h. The solution was partitioned between sat. NH4Cl and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (5/1 hexanes/EtOAc) to yield the title compound.

Workup

  1. stirringthe resulting solution was stirred at RT for 18 h
  2. customThe solution was partitioned between sat. NH4Cl and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (5/1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-c876f4a87b964f708ee43c9779f5f054
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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