Dichloromethane → HCID 22388590, compound

HRID 1072684Notes

Reaction equation

HRID 1072684 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]([O:6][CH:7]([CH3:16])[CH2:8][NH:9][S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[CH:4][CH:3]=1.[CH:19]1(B(O)O)[CH2:23][CH2:22][CH2:21]C1.C(Cl)Cl.[OH-:30].[Na+].[CH2:32]1[CH2:36][O:35][CH2:34][CH2:33]1>>[CH3:14][CH:13]([S:10]([NH:9][CH2:8][CH:7]([O:6][C:5]1[CH:17]=[CH:18][C:2]([C:22]2[CH:21]=[CH:32][C:36]([O:35][CH:34]([CH3:33])[CH2:8][NH:9][S:10]([CH:13]([CH3:15])[CH3:14])(=[O:11])=[O:30])=[CH:19][CH:23]=2)=[CH:3][CH:4]=1)[CH3:16])(=[O:12])=[O:11])[CH3:15]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 2734327Cyclopentylboronic acidHCID 9840705HCID 9840705, compound

Product 1

HCID 22388590HCID 22388590, compound

Conditions

Temperature
65 °C

Procedure

[2-(4-Bromophenoxy)propyl][(methylethyl)sulfonyl]amine (200 mg, 0.595 mmol), cyclopentylboronic acid (60 mg, 0.714 mmol), ([1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (4 mg, 0.024 mmol), and 2M sodium hydroxide (1 mL) were combined with THF (4 mL) in a 15 ml round-bottomed flask, fitted with a condenser, and stirbar, in a temperature regulated oil bath, and refluxed at 65° C. overnight in a nitrogen system. After cooling to room temperature, the reaction mixture was quenched with 15 mL of water, and extracted three times with 15 mL ethyl acetate. The organic extractions were combined and dried with magnesium sulfate, then filtered through Celite®, and concentrated in-vacuo, yielding 210 mg viscous black oil. This material was further purified using a 4000 uM rotor on a Chromatotron in a 1:1 hexanes:ethyl acetate solvent system to provide the title compound (50 mg, 16%) as white crystals.

Workup

  1. customfitted with a condenser
  2. temperatureAfter cooling to room temperature
  3. customthe reaction mixture was quenched with 15 mL of water
  4. extractionextracted three times with 15 mL ethyl acetate
  5. extractionThe organic extractions
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered through Celite®
  8. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-09fbf72c089d4127ab34d73aa2ba2510
Source dataset
uspto-grants-2005_06
Patent number
US06911476B2

Reaction notes

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