Boron tribromide → HCID 58065479, compound

HRID 1964620Notes

Reaction equation

HRID 1964620 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@@H:27]([CH3:30])[CH2:28][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@@H:27]([CH3:30])[CH2:28][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])[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 58065437HCID 58065437, compound

Product 1

HCID 58065479HCID 58065479, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(azetidin-1-ylcarbonyl)-3-chloro-2-(3-[(1S)-2-methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)pyridine (320 mg, 0.610 mmol) synthesized in Example 74 was dissolved in dichloromethane (10 mL), and boron tribromide (1.0 mol/L dichloromethane solution, 0.92 mL, 0.92 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 (165 mg, yield 53%) as a yellow 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-4ff5845cdbd0491595f9aa93f81d0e62
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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