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Boron tribromide → HCID 76321959, 화합물

HRID 1972553
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HRID 1972553 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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

생성물 1

HCID 76321959HCID 76321959, 화합물수율 86.1%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 516892Sodium Bicarbonate용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ff2c7d4ae53d4325aece750988827b68
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431563B2

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