Trimethylsilyl iodide → HCID 178424150, compound

HRID 2389370Notes

Reaction equation

HRID 2389370 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:5][N:4]=1.I[Si](C)(C)C>C(Cl)Cl.[Cl-].[Na+].O>[CH3:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[N:4][CH:5]=1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 68538705HCID 68538705, compound

Product 1

HCID 178424150HCID 178424150, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-methoxy-5-(2′-methylbiphenyl-2-yl)pyridine (2.20 g) in DCM (50 mL) was added iodo(trimethyl) silane (5.0 g) at ambient temperature. The reaction mixture was stirred at ambient temperature for 4 days. To the reaction mixture was added brine (50 mL). The mixture was extracted with EtOAc and the organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (EtOAc:chloroform=3:7) to afford 5-(2′-methylbiphenyl-2-yl)pyridin-2-ol (1.35 g) as pale yellow crystals.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialthe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (EtOAc:chloroform=3:7)

Sources & evidence

ORD record
ord-1aed091632664b479859c8ab6ad3cc92
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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