Boron tribromide → HCID 58065529, compound

HRID 1964736Notes

Reaction equation

HRID 1964736 reaction equation
C[O:2][CH2:3][C@H:4]([CH3:39])[O:5][C:6]1[CH:7]=[C:8]([CH:25]=[C:26]([C:28]2[NH:29][C:30]([C:33]3[O:34][C@@H:35]([CH3:38])[CH2:36][N:37]=3)=[CH:31][CH:32]=2)[CH:27]=1)[O:9][C:10]1[CH:15]=[N:14][C:13]([C:16]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)=[O:17])=[CH:12][N:11]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:38][C@@H:35]1[O:34][C:33]([C:30]2[NH:29][C:28]([C:26]3[CH:27]=[C:6]([CH:7]=[C:8]([O:9][C:10]4[CH:15]=[N:14][C:13]([C:16]([N:18]5[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]5)=[O:17])=[CH:12][N:11]=4)[CH:25]=3)[O:5][C@@H:4]([CH3:39])[CH2:3][OH:2])=[CH:32][CH:31]=2)=[N:37][CH2:36]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 58065431HCID 58065431, compound

Product 1

HCID 58065529HCID 58065529, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)-5-[(4-methylpiperazin-1-yl)carbonyl]pyrazine (259 mg, 0.48 mmol) synthesized in Example (131d) was dissolved in methylene chloride (15 mL), and boron tribromide (1.0 mol/L methylene chloride solution, 0.81 mL, 0.81 mmol) was added at −78° C. Subsequently, the temperature was brought back to room temperature, followed by stirring for 3 hours. To the reaction solution, a saturated aqueous sodium hydrogencarbonate solution was added, 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: methanol/methylene chloride=2%-8%) to afford the desired compound (62.4 mg, yield 25%) as a white solid.

Workup

  1. customwas brought back to room temperature
  2. extractionextraction
  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: methanol/methylene chloride=2%-8%)

Sources & evidence

ORD record
ord-70e048eac75b42d49607620c684e2eb4
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

Loading…