Sodium hydride → HCID 19627074, compound

HRID 446248Notes

Reaction equation

HRID 446248 reaction equation
[H-].[Na+].[N:3]1([CH2:8][CH2:9][OH:10])[CH2:7][CH2:6][CH2:5][CH2:4]1.F[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=1[N+:22]([O-])=O>C1COCC1>[N:3]1([CH2:8][CH2:9][O:10][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[NH2:22])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 762881-Pyrrolidineethanol

Product 1

HCID 19627074HCID 19627074, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (60%, 248 mg, 6.21 mmol) in dry THF was added 2-Pyrrolidin-1-yl-ethanol (0.68 mL, 5.74 mmol). Bubbling was observed. The reaction was stirred for 5 minutes, at which time 1-Fluoro-2-nitro-4-trifluoromethyl-benzene (0.67 mL, 4.79 mmol) was added. The solution turned red, and LCMS indicated completion of the reaction. The reaction was quenched by addition of H2O, and the mixture was extracted with EtOAc, dried with MgSO4, filtered, and concentrated to afford the title compound as an orange oil.

Workup

  1. customBubbling
  2. additionwas added
  3. customcompletion of the reaction
  4. customThe reaction was quenched by addition of H2O
  5. extractionthe mixture was extracted with EtOAc
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-50f3ff9f854c4669953e9e70c526cdc5
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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