Hydrochloric Acid → 6-((Tert-butyldiphenylsilyloxy)methyl)-3-(2-fluoro-5-methoxyphenyl)-2-neopentylpyridine

HRID 709632Notes

Reaction equation

HRID 709632 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[N:25]=[C:24](Cl)[C:23]([C:27]2[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=2[F:35])=[CH:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:36][C:37]([CH3:42])([CH3:41])[CH2:38][Mg]Cl.Cl>CC(C1C=CC=C(C(C)C)C=1N1[C-]=[N+](C2C(C(C)C)=CC=CC=2C(C)C)CC1)C.C1COCC1.C(OCC)C>[Si:1]([O:18][CH2:19][C:20]1[N:25]=[C:24]([CH2:36][C:37]([CH3:42])([CH3:41])[CH3:38])[C:23]([C:27]2[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=2[F:35])=[CH:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 1317338986-((Tert-butyldiphenylsilyloxy)methyl)-2-chloro-3-(2-fluoro-5-methoxyphenyl)pyridineHCID 178418809HCID 178418809, compound

Product 1

HCID 1317338996-((Tert-butyldiphenylsilyloxy)methyl)-3-(2-fluoro-5-methoxyphenyl)-2-neopentylpyridine

Reagents, catalysts & solvents 3

HCID 10883669SIPrCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, to a solution of 6-((tert-butyldiphenylsilyloxy)methyl)-2-chloro-3-(2-fluoro-5-methoxyphenyl)pyridine (10.0 g) and PEPPSIT™-SIPr catalyst (trade name) (1.33 g) in THF (100 mL) was added a 1.5 M solution of 2,2-dimethylpropylmagnesium chloride in diethyl ether (50 mL), and the mixture was stirred at room temperature for 16 hr. 1N Hydrochloric acid was added to the reaction mixture at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (10.0 g) as a crude brown oil. 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 saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e427650e9ba5479fb44aae0246b537d8
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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