2-Amino-3-bromopyridine → HCID 58056714, compound

HRID 561050Notes

Reaction equation

HRID 561050 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=O)[CH2:17]Br)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[C:26]([Br:27])=[CH:25][CH:24]=[CH:23][N:22]=1>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[N:20]=[C:21]2[C:26]([Br:27])=[CH:25][CH:24]=[CH:23][N:22]2[CH:17]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8177002-Amino-3-bromopyridineHCID 54423887HCID 54423887, compound

Product 1

HCID 58056714HCID 58056714, compoundYield 153.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

(S)-benzyl-2-(2-bromoacetyl)pyrrolidine-1-carboxylate (1.771 g, 5.4 mmol), 2-amino-3-bromo-pyridine (0.9412 g, 5.4 mmol), and ethanol (20 mL) were combined under nitrogen. The reaction mixture was heated to 78° C. and stirred overnight. The sample was concentrated and saturated sodium bicarbonate (50 mL) was added. The mixture was extracted with ethyl acetate (3×50 mL). The ethyl acetate extracts were dried over magnesium sulfate and filtered. The crude material was adsorbed onto silica gel and purified by flash chromatography (40 g SiO2, 0-100% ethyl acetate in hexanes) to give (S)-benzyl-2-(8-bromoimidazo[1,2-a]pyridin-2-yl)pyrrolidine-1-carboxylate (0.869 g, 8.3 mmol, 2.2 mmol, 40%).

Workup

  1. concentrationThe sample was concentrated
  2. additionsaturated sodium bicarbonate (50 mL) was added
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. dry with materialThe ethyl acetate extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. custompurified by flash chromatography (40 g SiO2, 0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2bae2ffda9d54111bf0fd44f1706e4f5
Source dataset
uspto-grants-2011_11
Patent number
US08063218B2

Reaction notes

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