Diethylethanolamine → Tert-butyl 6-(2-(n,n-diethylamino)eth-1-yloxy)picolinate

HRID 2121362Notes

Reaction equation

HRID 2121362 reaction equation
[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][OH:8])[CH2:4][CH3:5].[H-].[Na+].Br[C:12]1[N:17]=[C:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:15]=[CH:14][CH:13]=1>CN(C)C=O>[CH2:2]([N:3]([CH2:6][CH2:7][O:8][C:12]1[N:17]=[C:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:15]=[CH:14][CH:13]=1)[CH2:4][CH3:5])[CH3:1]

Participants

5

Reactant 3

HCID 7497DiethylethanolamineHCID 24758Sodium hydrideHCID 23432991tert-Butyl 6-bromopicolinate

Product 1

HCID 23433087Tert-butyl 6-(2-(n,n-diethylamino)eth-1-yloxy)picolinateYield 25.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.03 g of diethylaminoethanol were introduced into 25 ml of dimethylformamide. At room temp., 0.22 g (9.26 mmol) of sodium hydride (60% suspension in white oil) was added. After stirring at room temp. for 30 minutes, a solution of 2.03 g (8.882 mmol) of tert-butyl 6-bromopicolinate in 20 ml of dimethylformamide was added dropwise. The reaction mixture was stirred at room temp. for 16 hours. After decomposition of excess sodium hydride with water, the reaction mixture was concentrated in vacuo. The residue was purified by flash chromatography (toluene/tetrahydrofuran/methanol, 4/1/1+2.5% triethylamine). 0.67 g of a pale brown oil was obtained.

Workup

  1. stirringThe reaction mixture was stirred at room temp. for 16 hours
  2. concentrationAfter decomposition of excess sodium hydride with water, the reaction mixture was concentrated in vacuo
  3. customThe residue was purified by flash chromatography (toluene/tetrahydrofuran/methanol, 4/1/1+2.5% triethylamine)

Sources & evidence

ORD record
ord-a74c28d621bc4eb1b8958a97576a1302
Source dataset
uspto-grants-2004_02
Patent number
US06696437B1

Reaction notes

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