Water → HCID 89526079, compound

HRID 1620983Notes

Reaction equation

HRID 1620983 reaction equation
[H-].[Na+].[F:3][C:4]([F:15])([F:14])[C:5]1[N:10]=[CH:9][C:8]([CH2:11][C:12]#[N:13])=[CH:7][CH:6]=1.Br[CH2:17][CH2:18][CH2:19]Br.O>CS(C)=O.C1COCC1>[F:15][C:4]([F:14])([F:3])[C:5]1[N:10]=[CH:9][C:8]([C:11]2([C:12]#[N:13])[CH2:19][CH2:18][CH2:17]2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-

Product 1

HCID 89526079HCID 89526079, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (567 mg, 14.2 mmol, 60%) in DMSO (30 mL) was added dropwise a solution of Example 85D (1.2 g, 6.45 mmol) in THF (5 mL) at room temperature and then the mixture was stirred for 30 minutes, followed by the addition of a solution of 1,3-dibromopropane (1.4 g, 7.10 mmol) in THF (5 mL) at room temperature. The mixture was stirred for additional 2 hours. After addition of water (30 mL) carefully, the resulting mixture was extracted with EtOAc (30 mL×2). The combined organic layers were washed with water (30 mL) and brine (30 mL), dried over Na2SO4, filtered, and concentrated to provide the title compound (1.45 g, 6.45 mmol, yield 100%) as a oil. The crude product was used in the next step without further purification. LC-MS: m/z 227.2 (M+H)+.

Workup

  1. stirringThe mixture was stirred for additional 2 hours
  2. extractionthe resulting mixture was extracted with EtOAc (30 mL×2)
  3. washThe combined organic layers were washed with water (30 mL) and brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3bd18c73fea2483391c6b0ef22e4bbe2
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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