Sodium Chloride → HCID 58817759, compound

HRID 1986912Notes

Reaction equation

HRID 1986912 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 (3x'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 is 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 (3x's)
  7. washwash with water and brine
  8. customDry the
  9. extractionextract (MgSO4)
  10. concentrationconcentrate

Sources & evidence

ORD record
ord-2ce30b0a11ee4b7f98d51b4abdc79fae
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Reaction notes

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