Iodoethane → HCID 21257568, compound

HRID 636302Notes

Reaction equation

HRID 636302 reaction equation
[H-].[Na+].[C:3]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH2:18](I)[CH3:19]>CN(C=O)C>[C:3]([N:10]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=1)[CH2:18][CH3:19])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 11367776tert-Butyl (6-methylpyridin-2-yl)carbamate

Product 1

HCID 21257568HCID 21257568, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (60% dispersion in mineral oil, 1.15 g, 29.5 mmol) in DMF (50 mL) at 0° C. was added a solution of 2-(N-Boc-amino)-6-picoline in DMF (30 mL). The reaction was stirred at 0° C. for 15 min; then ethyl iodide (4.6 g, 30 mmol) was added. The reaction mixture was stirred at RT overnight; then was concentrated in vacuum. The residue was diluted with H2O and extracted with CH2Cl2 (3×50 mL). Drying (MgSO4), concentration, and silica gel chromatography (20% EtOAc/hexane) gave the title compound as colorless oil: MS (ES) m/e 237 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at RT overnight
  2. concentrationthen was concentrated in vacuum
  3. additionThe residue was diluted with H2O
  4. extractionextracted with CH2Cl2 (3×50 mL)
  5. customDrying
  6. concentration(MgSO4), concentration, and silica gel chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-a91f69fd57a341339d9c422baca2710a
Source dataset
uspto-grants-2001_02
Patent number
US06191304B1

Reaction notes

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