2,6-Lutidine → 5-Bromo-2-(1-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)pyridine

HRID 385733Notes

Reaction equation

HRID 385733 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[N:6][CH:7]=1.N1C(C)=CC=CC=1C.[Si:20](OS(C(F)(F)F)(=O)=O)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:11][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])([CH3:9])[CH3:10])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 154863922-(5-Bromopyridin-2-yl)propan-2-ol

Product 1

HCID 595263745-Bromo-2-(1-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(5-bromopyridin-2-yl)propan-2-ol (1.20 g, 5.55 mmol, prepared according to the method in Tetrahedron Lett. 2000, 41, 4335) and 2,6-lutidine (1.29 mL, 11.11 mmol) in CH2Cl2 (12 mL) was added TBSOTf (1.91 mL, 8.33 mmol). After stirring at room temperature for 2 h, the reaction was diluted with water and extracted with CH2Cl2 (2×). The combined organic layers were dried (MgSO4), filtered, and evaporated. The crude residue was purified on silica gel (0-10% EtOAc/hexanes) which afforded the title compound as a colorless oil.

Workup

  1. extractionextracted with CH2Cl2 (2×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude residue was purified on silica gel (0-10% EtOAc/hexanes) which

Sources & evidence

ORD record
ord-9667333d05d043c09bb65671686f6a71
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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