Tetrahydrofuran → Ethyl 3-(5-bromopicolinamido)propanoate

HRID 405108Notes

Reaction equation

HRID 405108 reaction equation
CN(C([O:8]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1.[Br:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]([OH:39])=O)=[N:35][CH:36]=1.CC[N:42]([CH:46](C)C)C(C)C>CCOC(C)=O>[Br:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]([NH:42][CH2:46][CH2:26][C:27]([O:28][CH2:29][CH3:25])=[O:8])=[O:39])=[N:35][CH:36]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 6085445-Bromopyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 62959749Ethyl 3-(5-bromopicolinamido)propanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Solid HATU (3.8 g, 9.9 mmol) was added to a THF solution (100 mL) of 5-bromopicolinic acid (2.0 g, 9.9 mmol), i-Pr2NEt (5.2 mL, 29.7 mmol), and (3-alanine ethyl ester hydrochloride (1.7 g, 10.9) and the resulting mixture was warmed to 45° C. After 16 h the resulting mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-a9ea27d954cb4db6912c8798715a2729
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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