Sodium Bicarbonate → tert-butyl {(1S)-2-[4-(6-ethoxy-3-fluoropyrazolo[1,5-a]pyridin-2-yl)phenoxy]-1-methylethyl}carbamate

HRID 1026320Notes

Reaction equation

HRID 1026320 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([N:10]=[C:11]([C:13]3[CH:30]=[CH:29][C:16]([O:17][CH2:18][C@@H:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:20])=[CH:15][CH:14]=3)[CH:12]=2)[CH:9]=1)[CH3:2].[F:31][B-](F)(F)F.F[B-](F)(F)F.F[N+]1C=CC=CC=1C1C=CC=C[N+]=1F.C(=O)([O-])O.[Na+]>C(#N)C>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([N:10]=[C:11]([C:13]3[CH:30]=[CH:29][C:16]([O:17][CH2:18][C@@H:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])[CH3:20])=[CH:15][CH:14]=3)[C:12]=2[F:31])[CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27339311,1'-Difluoro-2,2'-bipyridinium Bis(tetrafluoroborate)HCID 86666306tert-butyl {(1S)-2-[4-(6-ethoxypyrazolo[1,5-a]pyridin-2-yl)phenoxy]-1-methylethyl}carbamate

Product 1

HCID 86666308tert-butyl {(1S)-2-[4-(6-ethoxy-3-fluoropyrazolo[1,5-a]pyridin-2-yl)phenoxy]-1-methylethyl}carbamateYield 30.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of tert-butyl {(1S)-2-[4-(6-ethoxypyrazolo[1,5-a]pyridin-2-yl)phenoxy]-1-methylethyl}carbamate (400 mg), 1,1′-difluoro-2,2′-bipyridinium bis(tetrafluoroborate) (358 mg) and acetonitrile (3 mL) was stirred at room temperature for 3 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The separated organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as colorless crystals (129 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe separated organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f01fec0313724749acbdd72e49325091
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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