Isopropanol → HCID 59367711, compound

HRID 515562Notes

Reaction equation

HRID 515562 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[N:4][CH:3]=1.[F:8][C:9]1[CH:19]=[CH:18][C:12]([C:13](OCC)=[O:14])=[CH:11][CH:10]=1.C[Si](C)(C)N[Si](C)(C)C.[Na].[Cl-].[NH4+].C(O)(C)C>O1CCCC1.C(OC(C)C)(C)C>[F:8][C:9]1[CH:19]=[CH:18][C:12]([C:13](=[O:14])[CH2:1][C:2]2[CH:7]=[CH:6][N:5]=[N:4][CH:3]=2)=[CH:11][CH:10]=1

Participants

8

Reactant 5

HCID 3776IsopropanolHCID 25517Ammonium ChlorideHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 1368824-MethylpyridazineHCID 45051731Sodium hexamethyidisilazane

Product 1

HCID 59367711HCID 59367711, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 7914Diisopropyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution under argon of 1.88 g (20.0 mmol) of 4-methylpyridazine and 3.36 g (20.0 mmol) of ethyl 4-fluorobenzoate in 50 ml of anhydrous tetrahydrofuran is cooled to 0° C. and then 20.0 ml (40.0 mmol) of a 2M solution of sodium hexamethyldisilazane in tetrahydrofuran (THF) are added dropwise. After the addition, the temperature is allowed to return to ambient temperature, while a gradual setting of the reaction medium is observed. After one hour, the mixture is poured into an aqueous solution of ammonium chloride and the product is extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated under reduced pressure to give an orangey-red solid. The latter is triturated at reflux in 80 ml of diisopropyl ether containing a few ml of isopropyl alcohol and the solid is then isolated by filtration after cooling to 0° C. 3.35 g of a pale yellow powder are thus isolated after drying.

Workup

  1. additionAfter the addition
  2. customto return to ambient temperature, while a gradual setting of the reaction medium
  3. extractionthe product is extracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give an orangey-red solid
  8. customThe latter is triturated
  9. customthe solid is then isolated by filtration

Sources & evidence

ORD record
ord-60a88cae06454454b9f16626718bdf54
Source dataset
uspto-grants-2015_08
Patent number
US09108971B2

Reaction notes

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