Triethylamine → HCID 58201199, compound

HRID 2093550Notes

Reaction equation

HRID 2093550 reaction equation
[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH3:10])[C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl>[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH3:10])[C:5]([CH2:8][O:9][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 582011981209459-79-9

Product 1

HCID 58201199HCID 58201199, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The above (5-bromo-4-methoxy-3-methylpyridin-2-yl)methanol (500 mg) was dissolved in dichloromethane (10 ml), and t-butyldimethylsilyl chloride (487 mg), triethylamine (0.48 ml), and dimethylaminopyridine (30 mg) were then added to the solution under cooling in an ice bath. The resulting mixture was stirred at room temperature overnight. Thereafter, the reaction solution was diluted with dichloromethane, and was then washed with a saturated sodium bicarbonate solution. The organic layer was dried over anhydrous sodium sulfate, and the filtrate was then concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain the title compound (743 mg) as an oily substance.

Workup

  1. temperatureunder cooling in an ice bath
  2. washwas then washed with a saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationthe filtrate was then concentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-06832b2564f3455b8d83563cda483936
Source dataset
uspto-grants-2013_05
Patent number
US08445504B2

Reaction notes

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