Sodium hydride → HCID 58153380, compound

HRID 508462Notes

Reaction equation

HRID 508462 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[H-].[Na+].[Br:15][C:16]1[C:17](Cl)=[N:18][C:19]([CH3:25])=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1>C[Si](C)(C)N[Si](C)(C)C.O1CCOCC1>[Br:15][C:16]1[C:17]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:9]([F:10])([F:11])[F:12])[CH:4]=2)=[N:18][C:19]([CH3:25])=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 805204-Chloro-3-(trifluoromethyl)phenolHCID 299193693-Bromo-2-chloro-6-methyl-5-nitropyridine

Product 1

HCID 58153380HCID 58153380, compoundYield 18.9%

Reagents, catalysts & solvents 2

HCID 13838HexamethyldisilazaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

In a 50 mL single-necked round-bottomed flask, 0.13 ml of hexamethyldisilazane and 1.21 g of 4-chloro-3-trifluoromethyl-phenol are dissolved and stirred in 3.0 ml of dry dioxane under Argon atmosphere at ambient temperature. To this mixture, 270 mg of 55% sodium hydride suspension is added carefully (gas evolution) and stirring is continued for 30 minutes. After this, a solution of 1.55 g of 3-bromo-2-chloro-6-methyl-5-nitro-pyridine in 4.0 ml of dry dioxane is added dropwise by syringe and stirring is continued for 22 hours at ambient temperature. The reaction is then quenched by the addition of an excess of a dilute aqueous NaOH solution (pH=12 of water phase) and extraction carried out with cyclohexane. The organic phase is dried over sodium sulfate, filtered and concentrated in vacuo to obtain an orange oil. Purification by flash chromatography over a silica gel cartridge (50 g, 150 ml) using heptane/ethyl acetate 95:5 (v:v) as eluent gave 480 mg of the compound in the form of a wet solid.

Workup

  1. stirringstirring
  2. waitis continued for 22 hours at ambient temperature
  3. customThe reaction is then quenched by the addition of an
  4. extractionexcess of a dilute aqueous NaOH solution (pH=12 of water phase) and extraction
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto obtain an orange oil
  9. customPurification by flash chromatography over a silica gel cartridge (50 g, 150 ml)

Sources & evidence

ORD record
ord-82bedc1225ea4b84bffc4a1fe8f17c5b
Source dataset
uspto-grants-2015_08
Patent number
US09096525B2

Reaction notes

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