Ethyl Acetate → (2S)-2-{3-[4-(Methylsulfonyl)phenoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}propan-1-ol

HRID 1964498Notes

Reaction equation

HRID 1964498 reaction equation
C[O:2][CH2:3][C@H:4]([CH3:33])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]3[S:29][CH:30]=[CH:31][N:32]=3)=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:11]=1.B(Br)(Br)Br.ClCCl.C(=O)([O-])O.[Na+].C(OCC)(=O)C>ClCCl>[CH3:22][S:19]([C:16]1[CH:15]=[CH:14][C:13]([O:12][C:10]2[CH:11]=[C:6]([CH:7]=[C:8]([C:23]3[NH:27][C:26]([C:28]4[S:29][CH:30]=[CH:31][N:32]=4)=[CH:25][CH:24]=3)[CH:9]=2)[O:5][C@@H:4]([CH3:33])[CH2:3][OH:2])=[CH:18][CH:17]=1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 580654642-(5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-1,3-thiazole

Product 1

HCID 58065533(2S)-2-{3-[4-(Methylsulfonyl)phenoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}propan-1-olYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, 2-(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-1,3-thiazole (88.8 mg, 0.183 mmol) synthesized in Example (1i) was dissolved in dichloromethane (5 mL), and a boron tribromide/dichloromethane solution (1.0M, 220 μL, 0.22 mmol) was added at −78° C. Subsequently, the temperature was brought back to room temperature, followed by stirring for 30 minutes. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and extraction was carried out with ethyl acetate. The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-50%) to afford the desired compound (52.2 mg, yield 61%) as a pale yellow solid.

Workup

  1. customwas brought back to room temperature
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-50%)

Sources & evidence

ORD record
ord-abd272cdd197401f8fbc0119b9b92cba
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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