Hexane → tert-butyl {(1S)-2-[4-(6-ethoxy-7-fluoropyrazolo[1,5-a]pyridin-2-yl)phenoxy]-1-methylethyl}carbamate

HRID 1026321Notes

Reaction equation

HRID 1026321 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].CCCCCC.C([Li])CCC.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:52])(=O)=O)=CC=1>C1COCC1.O>[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)[CH:12]=2)[C:9]=1[F:52])[CH3:2]

Participants

7

Reactant 4

HCID 8058HexaneHCID 588007N-FluorobenzenesulfonimideHCID 86666306tert-butyl {(1S)-2-[4-(6-ethoxypyrazolo[1,5-a]pyridin-2-yl)phenoxy]-1-methylethyl}carbamateHCID 178418339Butyllithium

Product 1

HCID 123362978tert-butyl {(1S)-2-[4-(6-ethoxy-7-fluoropyrazolo[1,5-a]pyridin-2-yl)phenoxy]-1-methylethyl}carbamateYield 30.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl {(1S)-2-[4-(6-ethoxypyrazolo[1,5-a]pyridin-2-yl)phenoxy]-1-methylethyl}carbamate (580 mg) in THF (10 mL) was added dropwise a hexane solution (1.6 M, 2.2 mL) of n-butyllithium at −78° C. under an argon atmosphere, and the mixture was stirred for 1.5 hr. To the reaction mixture was added N-fluorobenzenesulfonimide (578 mg) at −78° C., and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with 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 a pale-yellow solid (187 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-420c34f6bc1c442bb4aa6017a7150869
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

Loading…