Hydrochloric Acid → 5-(((Tert-butyldimethylsilyl)oxy)methyl)-2-(2-fluoro-5-methoxyphenyl)-3-neopentylpyridine

HRID 709780Notes

Reaction equation

HRID 709780 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([C:22]2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=2[F:30])=[N:9][CH:10]=[C:11]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH:12]=1)(=O)=O.[CH2:33]([Mg]Cl)[C:34]([CH3:37])([CH3:36])[CH3:35].Cl>C1COCC1.C(OCC)C.CC(C1C=CC=C(C(C)C)C=1N1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C1)C.C1C=NC=C(Cl)C=1.Cl[Pd]Cl>[Si:15]([O:14][CH2:13][C:11]1[CH:12]=[C:7]([CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:8]([C:22]2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=2[F:30])=[N:9][CH:10]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 1317339185-(((Tert-butyldimethylsilyl)oxy)methyl)-2-(2-fluoro-5-methoxyphenyl)pyridin-3-yl trifluoromethanesulfonateHCID 178418809HCID 178418809, compound

Product 1

HCID 1317339195-(((Tert-butyldimethylsilyl)oxy)methyl)-2-(2-fluoro-5-methoxyphenyl)-3-neopentylpyridine

Reagents, catalysts & solvents 3

HCID 16218181Dichloro-[1,3-bis(diisopropylphenyl)-2-imidazolidinyliden]-(3-chloropyridyl)palladium(II)CatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, to a solution of 5-(((tert-butyldimethylsilyl)oxy)methyl)-2-(2-fluoro-5-methoxyphenyl)pyridin-3-yl trifluoromethanesulfonate (2.72 g) and PEPPSI-SIPr (trade name) (374 mg) in THF (25 mL) was added dropwise a 1.0 M solution (24 mL) of neopentylmagnesium chloride in diethyl ether, and the mixture was stirred at room temperature for 10 min. 1N Hydrochloric acid was added at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound. This compound was used for the next step without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-35a2fb79524542b0bbb140bb23afff28
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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