Boron tribromide → HCID 76321959, compound

HRID 1972553Notes

Reaction equation

HRID 1972553 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)(=[O:23])=[O:22])[CH2:17][CH:16]2[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([O:36]C)[CH:31]=2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].B(Br)(Br)Br>ClCCCl.C([O-])(O)=O.[Na+]>[F:39][C:2]([F:1])([F:38])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)(=[O:23])=[O:22])[CH2:17][CH:16]2[CH2:29][C:30]2[CH:31]=[C:32]([OH:36])[CH:33]=[CH:34][CH:35]=2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 866703961,1,1,3,3,3-Hexafluoro-2-(4-(2-(3-methoxybenzyl)-4-(thiophen-2-ylsulfonyl)piperazin-1-yl)phenyl)-2-propanol

Product 1

HCID 76321959HCID 76321959, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

To a 50-mL round-bottomed flask was added 1,1,1,3,3,3-hexafluoro-2-(4-(2-(3-methoxybenzyl)-4-(thiophen-2-ylsulfonyl)piperazin-1-yl)phenyl)propan-2-ol (38 mg, 0.064 mmol, Example 175) and BBr3 (0.025 mL, 0.256 mmol, Aldrich, St. Louis, Mo.) in DCE (3 mL). The reaction mixture was stirred at 80° C. for 2 h and then diluted with saturated NaHCO3 (20 mL) and extracted with EtOAc (2×30 mL). The organic extracts were washed with saturated aqueous NaCl (10 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow glass. The crude product was purified by silica gel chromatography, eluting with 40% EtOAc in hexanes to give 3-((1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-4-(thiophen-2-ylsulfonyl)piperazin-2-yl)methyl)phenol (32 mg) (racemic mixture) as a light-yellow tar.

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe organic extracts were washed with saturated aqueous NaCl (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated in vacuo
  6. customto give the crude material as a light-yellow glass
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with 40% EtOAc in hexanes

Sources & evidence

ORD record
ord-ff2c7d4ae53d4325aece750988827b68
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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