N-BOC-ethylenediamine → HCID 70810523, compound

HRID 734876Notes

Reaction equation

HRID 734876 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[N:6][CH:7]=1.[NH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 187201N-BOC-ethylenediamineHCID 5936905-Bromo-2-iodopyridine

Product 1

HCID 70810523HCID 70810523, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 8.86 g (31.20 mmol) of 5-bromo-2-iodopyridine and 10.00 g (62.42 mmol) of tert-butyl (2-aminoethyl)carbamate was stirred for 3 hours at 170° C. The reaction mixture was cooled to RT and diluted with EtOAc. The organic phase was washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, and evaporated down in vacuo. The crude product was purified by chromatography (silica gel, cyc/EtOAc 4:1). Yield: 2.37 g (24% of theoretical); C12H18BrN3O2 (M=316.194); calc.: molpeak (M+H)+:316/318 (Br); found: molpeak (M+H)+:316/318 (Br); Rf value: 0.22 (silica gel, cyc/EtOAc 2:1).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washThe organic phase was washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated down in vacuo
  5. customThe crude product was purified by chromatography (silica gel, cyc/EtOAc 4:1)

Sources & evidence

ORD record
ord-32f7b303981245d19f661140b55786fa
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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