Sodium hydride → HCID 131734684, compound

HRID 1772708Notes

Reaction equation

HRID 1772708 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[NH:13][N:12]=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:16][Si:17]([CH3:24])([CH3:23])[CH2:18][CH2:19][O:20][CH2:21]Cl>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[N:13]([CH2:21][O:20][CH2:19][CH2:18][Si:17]([CH3:24])([CH3:23])[CH3:16])[N:12]=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178419404HCID 178419404, compound

Product 1

HCID 131734684HCID 131734684, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of compound 63a (360 mg, 1.40 mmol) and 60% NaH (135 mg, 3.40 mmol) in DMF (2 mL) was stirred for 20 min at rt. At that time, 2-(trimethylsilyl) ethoxymethyl chloride (0.558 mL, 3.10 mmol) was added and the resulting mixture was stirred at rt for 12 h. The reaction mixture was diluted with DCM (300 mL) and washed with saturated NH4Cl solution (200 mL), water (200 mL) and brine (200 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (0-50% EtOAc/heptanes) to give compound 63b. Mass Spectrum LCMS, ESI (pos.) Calcd. for C14H20BrN3OSSi: 386.1 [M+H]. found 386.2.

Workup

  1. stirringthe resulting mixture was stirred at rt for 12 h
  2. washwashed with saturated NH4Cl solution (200 mL), water (200 mL) and brine (200 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel (0-50% EtOAc/heptanes)

Sources & evidence

ORD record
ord-199f0462e2da46bcb48b90e83b9fbfc0
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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