Sodium Chloride → HCID 58817759, compound

HRID 2111710Notes

Reaction equation

HRID 2111710 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:16]=3[S:17][C:18]=2Br)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CCCCCC.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:46])(=O)=O)=CC=1.[Na+].[Cl-]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:16]=3[S:17][C:18]=2[F:46])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 8058HexaneHCID 588007N-FluorobenzenesulfonimideHCID 58817714HCID 58817714, compoundHCID 178418339Butyllithium

Product 1

HCID 58817759HCID 58817759, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-65 °C

Procedure

At a temperature of −65° C. stir, under nitrogen, a solution of the 4-(2-bromo-6-fluoro-benzo[b]thiophen-3-yl)-piperazine-1-carboxylic acid tert-butyl ester (Example 28b) (15.59 g, 37.55 mmol) in anhydrous THF (247 mL) and add, dropwise, n-butyllithium in hexane (2.5M, 19.53 mL, 48.82 mmol). Stir for 30 min and then add, dropwise, N-fluorobenzenesulfonimide (17.76 g, 56.33 mmol) dissolved in anhydrous THF. Stir overnight at ambient temperature, cool the reaction to 0° C., add saturated NaCl solution and then water. Extract the mixture with EtOAc (3×'s), combine the extracts and wash with water and brine. Dry the extract (MgSO4), and concentrate to obtain 11.0 g of oil. Chromatograph the oil over silica gel (ether/pet. ether, 9:1) and obtain 6.28 g (52%) of red oil, MS, m/z, 354 (M+H)+.

Workup

  1. stirringStir for 30 min
  2. additionadd
  3. stirringStir overnight at ambient temperature
  4. temperaturecool
  5. customthe reaction to 0° C.
  6. extractionExtract the mixture with EtOAc (3×'s),
  7. washwash with water and brine
  8. customDry the
  9. extractionextract (MgSO4)
  10. concentrationconcentrate

Sources & evidence

ORD record
ord-710b66c9baf34bd9b8f31c79d9f7bd18
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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