Acetonitrile → HCID 57545990, compound

HRID 913948Notes

Reaction equation

HRID 913948 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([O:14][CH2:15][C:16]2([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:12]O)[C:8]2[C:4](=[CH:5][N:6]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[N:7]=2)[CH:3]=1.C(#N)C.C(N(C(C)C)CC)(C)C.F.F.F.C(N(C(C)C)CC)(C)C.[F:68]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.C([O-])(O)=O.[Na+]>CCOCC>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([O:14][CH2:15][C:16]2([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:18][CH2:17]2)[CH2:12][F:68])[C:8]2[C:4](=[CH:5][N:6]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:42])([CH3:43])[CH3:41])[N:7]=2)[CH:3]=1

Participants

8

Reactant 6

HCID 6342AcetonitrileHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 45108321N-Ethyl-N-(propan-2-yl)propan-2-amine--hydrogen fluoride (1/3)HCID 57545941HCID 57545941, compound

Product 1

HCID 57545990HCID 57545990, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of tert-butyl 4-((1-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)-2-hydroxyethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (440 mg, 0.694 mmol) in ACETONITRILE (0.1 mL, 1.915 mmol) at room temperature was added diisopropylethylamine (0.545 mL, 3.12 mmol), Diisopropylethylamine trihydrofluoride (197 mg, 1.041 mmol), and perfluoro-1-butanesulfonyl fluoride (0.249 mL, 1.387 mmol). The reaction was stirred at room temperature overnight. It was then poured into sat'd NaHCO3 and diluted with ether. The ether layer was washed with water and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel column chromatography (15%-20% EtOAc/Hex) to give title compound (420 mg, 0.660 mmol, 95% yield) as a colorless film. LC/MS (HPLC method 3): tR=4.33 min, 636.3(MH)+.

Workup

  1. washThe ether layer was washed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel column chromatography (15%-20% EtOAc/Hex)

Sources & evidence

ORD record
ord-955e444348f348848e66b46f4410944e
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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