Sodium Bicarbonate → 3-Oxa-8-azabicyclo[3.2.1]octan-8-yl(8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanone

HRID 931033Notes

Reaction equation

HRID 931033 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([C:12]([C:15]([OH:17])=O)=[CH:13][N:14]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH:43]12[NH:50][CH:47]([CH2:48][CH2:49]1)[CH2:46][O:45][CH2:44]2.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(N(CC)CC)C>[CH:47]12[N:50]([C:15]([C:12]3[N:4]4[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=[C:2]([Br:1])[C:3]4=[N:14][CH:13]=3)=[O:17])[CH:43]([CH2:49][CH2:48]1)[CH2:44][O:45][CH2:46]2

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534011293-Oxa-8-azabicyclo(3.2.1)octane hydrochlorideHCID 1183788958-Bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 1183789383-Oxa-8-azabicyclo[3.2.1]octan-8-yl(8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanoneYield 80.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (300 mg) in DMF (6 mL) were added HATU (443 mg) and triethylamine (0.311 mL), and the mixture was stirred at room temperature for 10 min. To the reaction mixture was added 3-oxa-8-azabicyclo[3.2.1]octane hydrochloride (160 mg), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (315 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-db3f840714894c83b7f35df7738bd4b2
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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