Boron tribromide → HCID 58065466, compound

HRID 909679Notes

Reaction equation

HRID 909679 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:11]=[CH:12][C:13]([C:16]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)=[O:17])=[N:14][CH:15]=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][CH: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 58065510HCID 58065510, compound

Product 1

HCID 58065466HCID 58065466, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-{[5-(3-[(1S)-2-Methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)pyridin-2-yl]carbonyl}-4-methylpiperazine (185 mg, 0.35 mmol) synthesized in Example (129g) was dissolved in methylene chloride (10 mL), and boron tribromide (1.0 mol/L methylene chloride solution, 694 μL, 0.694 mmol) was added at −78° C. Subsequently, the temperature was brought back to room temperature, followed by stirring for 50 minutes. 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=0%-10%) to afford the desired compound (51 mg, yield 28%) 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=0%-10%)

Sources & evidence

ORD record
ord-6a6e073100ef43dfb1ab15dc12e45702
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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