Boron tribromide → HCID 135977434, compound

HRID 1964617Notes

Reaction equation

HRID 1964617 reaction equation
[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([Cl:37])[C:10]([O:13][C:14]3[CH:19]=[C:18]([C:20]4[NH:21][C:22]([C:25]5[O:26][C:27]([CH3:30])=[N:28][N:29]=5)=[CH:23][CH:24]=4)[CH:17]=[C:16]([O:31][C@@H:32]([CH3:36])[CH2:33][O:34]C)[CH:15]=3)=[N:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.[Cl-].[NH4+]>ClCCl>[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([Cl:37])[C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:17]=[C:18]([C:20]4[NH:21][C:22]([C:25]5[O:26][C:27]([CH3:30])=[N:28][N:29]=5)=[CH:23][CH:24]=4)[CH:19]=3)[O:31][C@@H:32]([CH3:36])[CH2:33][OH:34])=[N:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 135977440HCID 135977440, compound

Product 1

HCID 135977434HCID 135977434, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(Azetidin-1-ylcarbonyl)-3-chloro-2-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}pyridine (370 mg, 0.706 mmol) synthesized in Example (71b) was dissolved in dichloromethane (10 mL), and boron tribromide (1.0 mol/L dichloromethane solution, 1.10 mL, 1.10 mmol) was added dropwise at −78° C., followed by stirring at room temperature for 1 hour under nitrogen atmosphere. To this reaction solution, a saturated aqueous ammonium chloride solution (20 mL) was added, and extraction was carried out with dichloromethane (20 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: methanol/dichloromethane=1%-3%) to afford the desired compound (205 mg, yield 57%) as a white solid.

Workup

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: methanol/dichloromethane=1%-3%)

Sources & evidence

ORD record
ord-993791f4a8e742fca67bfe2c77b43217
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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