Sodium Bicarbonate → N-(2-Chloroethyl)-5-{3-[(1S)-2-hydroxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxamide

HRID 1964533Notes

Reaction equation

HRID 1964533 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[NH:8][C:9]([C:12]2[CH:17]=[C:16]([O:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[CH:15]=[C:14]([O:29][C@@H:30]([CH3:34])[CH2:31][O:32]C)[CH:13]=2)=[CH:10][CH:11]=1)=[O:6].ClCCl.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[NH:8][C:9]([C:12]2[CH:17]=[C:16]([O:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[CH:15]=[C:14]([O:29][C@@H:30]([CH3:34])[CH2:31][OH:32])[CH:13]=2)=[CH:10][CH:11]=1)=[O:6]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 58092810N-(2-Chloroethyl)-5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxamide

Product 1

HCID 58092808N-(2-Chloroethyl)-5-{3-[(1S)-2-hydroxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxamideYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

N-(2-Chloroethyl)-5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxamide (88 mg, 0.17 mmol) synthesized in Example (18b) was dissolved in dichloromethane (5 mL), and cooled to −78° C., and a 1.0 mol/L boron tribromide dichloromethane solution (0.19 mL, 0.19 mmol) was added under nitrogen atmosphere. The temperature was raised naturally, the solution was stirred at room temperature for 30 minutes, subsequently a saturated aqueous sodium hydrogencarbonate solution was added to neutralize the reaction solution, and extraction was carried out with dichloromethane (60 mL). 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=50%-80%) to afford the desired product (55 mg, yield 64%) as a white solid.

Workup

  1. temperatureThe temperature was raised naturally
  2. extractionthe reaction solution, and extraction
  3. washThe organic layer was washed with saturated brine
  4. dry with materialsubsequently dried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified
  7. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=50%-80%)

Sources & evidence

ORD record
ord-ff760952b4c24bb4be5f9478b1309f20
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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