Ethylamine → HCID 23582255, compound

HRID 1180644Notes

Reaction equation

HRID 1180644 reaction equation
Br[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]([CH2:12][CH2:13][OH:14])=[CH:4][N:3]=1.[CH2:15]([NH2:17])[CH3:16]>CO.C1COCC1>[CH2:15]([NH:17][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]([CH2:12][CH2:13][OH:14])=[CH:4][N:3]=1)[CH3:16]

Participants

5

Reactant 2

HCID 6341Ethylamine2×HCID 23582254HCID 23582254, compound

Product 1

HCID 23582255HCID 23582255, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
57.5 °C

Procedure

7.85 g (30.18 mmol) of methyl 2-bromo-5-(2-hydroxyethyl)pyridine-3-carboxylate (free base) were dissolved in 20 ml MeOH and added to a 250 ml 3-neck-round bottom flask with a stirrer bar, a thermocouple, a addition funnel and a cold condenser (capable for −78° C.). The solution was treated with 433 mg (3.018 mmol, 0.1 equiv.) CuBr and heated to 55-60° C. The reaction mixture was treated dropwise with 74 ml (148 mmol, 4.9 equiv.) 2M EtNH2 in THF. The reaction was kept at 55-60° C. for two hour and monitored. If the chromatogram still shows starting material the reaction was treated with additional 20 ml (40 mmol, 1.32 equiv.) 2M EtNH2 in THF and kept another 2 h at 55-60° C.

Workup

  1. additionadded to a 250 ml 3-neck-round bottom flask with a stirrer bar
  2. customa thermocouple, a addition funnel and a cold condenser (capable for −78° C.)
  3. waitkept another 2 h at 55-60° C.

Sources & evidence

ORD record
ord-94e980483542451f91801a0e7807f0d3
Source dataset
uspto-grants-2007_10
Patent number
US07282583B2

Reaction notes

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