Triethylamine → HCID 58001760, compound

HRID 420740Notes

Reaction equation

HRID 420740 reaction equation
[Cl:1][C:2]1[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:4][CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1.CCN(CC)CC.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>CN(C=O)C.CC(OC)(C)C>[Cl:1][C:2]1[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:4][CH:5]=[C:6]([CH2:8][O:9][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 580017592-Pyridinecarboxylic acid, 3-chloro-5-(hydroxymethyl)-, methyl ester

Product 1

HCID 58001760HCID 58001760, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of methyl 3-chloro-5-(hydroxymethyl)-2-pyridinecarboxylate (332.6 mg, 1.650 mmol), Et3N (0.345 ml, 2.475 mmol), and tert-butyldimethylsilyl chloride (261 mg, 1.732 mmol) in DMF (4 ml) was stirred at room temperature for 3 h. The crude was diluted with TBME (40 ml) and organic phase was washed with water and brine. Combined organic phases were washed with sat NH4Cl, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound (488 mg, 84% yield) as yellow oil pure enough to be used in the next step.

Workup

  1. washwas washed with water and brine
  2. washCombined organic phases were washed with sat NH4Cl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-13a36546836941619b2ba7852e856aa5
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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