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Chlorotrimethylsilane → 3-(3-Chlorophenyl)-2-(difluoromethoxy)-5-(pyridin-2-ylmethyl)pyridine

HRID 2271480
Notes
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Reaction equation

HRID 2271480 reaction equation
[Br-].[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH2:19][Zn+])[CH:12]=[N:13][C:14]=2[O:15][CH:16]([F:18])[F:17])[CH:6]=[CH:7][CH:8]=1.BrCCBr.C[Si](Cl)(C)C.BrC[C:32]1[CH:33]=[C:34](C2C=CC=C(Cl)C=2)[C:35](OC(F)F)=[N:36][CH:37]=1>C1COCC1.[Zn]>[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2[C:14]([O:15][CH:16]([F:18])[F:17])=[N:13][CH:12]=[C:11]([CH2:19][C:35]3[CH:34]=[CH:33][CH:32]=[CH:37][N:36]=3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 904158565-(Bromomethyl)-3-(3-chlorophenyl)-2-(difluoromethoxy)pyridine2×HCID 178506410HCID 178506410, compound

Product 1

HCID 904171893-(3-Chlorophenyl)-2-(difluoromethoxy)-5-(pyridin-2-ylmethyl)pyridine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

((5-(3-Chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl)methyl)zinc(II) bromide. To a suspension of zinc (42.77 mg, 0.65 mmol) in THF (1 mL) was added 1,2-dibromoethane (2.48 μL, 0.03 mmol). The resulting mixture was heated at 70° C. for 10 minutes before being cooled to room temperature. Once cooled, trimethylsilylchloride (2.92 μL, 0.02 mmol) was added and the solution was stirred at room temperature for an additional 30 min. To the activated zinc solution was added 5-(bromomethyl)-3-(3-chlorophenyl)-2-(difluoromethoxy)pyridine (Intermediate 12, 200 mg, 0.57 mmol) and the resulting mixture was heated at 70° C. for 8 h. The reaction mixture was cooled to room temperature and decanted from the solids to afford a −0.5 M solution of the title compound.

Workup

  1. temperaturebefore being cooled to room temperature
  2. temperatureOnce cooled
  3. temperaturethe resulting mixture was heated at 70° C. for 8 h
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customdecanted from the solids

Sources & evidence

ORD record
ord-4d3f8e1260264b8c9fde89fbfbd648fa
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09120770B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes