Ethanolamine → HCID 23537282, compound

HRID 445567Notes

Reaction equation

HRID 445567 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](Cl)=[N:6][CH:7]=1.[OH:9][CH2:10][CH2:11][NH2:12]>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][CH2:11][CH2:10][OH:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 23537282HCID 23537282, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 5-bromo-2-chloropyridine (Aldrich, Buchs, Switzerland, 1 g, 5.2 mmol) and 2-hydroxyethylamine (1.59 g, 26 mmol) in 3 ml DMA was heated by microwaves at 170° C. for 1 h. Then the RM was quenched with saturated aqueous NaHCO3 (50 ml) and extracted with EtOAc. The organic layers were washed with saturated aqueous NaHCO3 (4×), dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (DCM/MeOH 0 to 5%). The fractions containing product were evaporated together to give the title compound as an off-white solid. (HPLC: tR 1.66 min (Method A); M+H=217, 219 (Br-pattern) MS-ES)

Workup

  1. customThen the RM was quenched with saturated aqueous NaHCO3 (50 ml)
  2. extractionextracted with EtOAc
  3. washThe organic layers were washed with saturated aqueous NaHCO3 (4×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (DCM/MeOH 0 to 5%)
  8. additionThe fractions containing product
  9. customwere evaporated together

Sources & evidence

ORD record
ord-b90de31bc5f44319b2bdde14139fdef7
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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