Tetrahydrofuran → Tert-butyl 3-(5-bromopicolinamido)propanoate

HRID 405112Notes

Reaction equation

HRID 405112 reaction equation
[CH3:1][N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]1COCC1.[Br:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]([OH:39])=O)=[N:35][CH:36]=1.CCN([CH:46]([CH3:48])[CH3:47])C(C)C.CC[O:51][C:52]([CH3:54])=[O:53]>>[Br:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]([NH:2][CH2:1][CH2:54][C:52]([O:51][C:46]([CH3:47])([CH3:48])[CH3:25])=[O:53])=[O:39])=[N:35][CH:36]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 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 71060050Tert-butyl 3-(5-bromopicolinamido)propanoate

Procedure

Solid HATU (4.0 g, 10.6 mmol) was added to a THF solution (100 mL) of 5-bromopicolinic acid (2.1 g, 10.6 mmol), i-Pr2NEt (7.4 mL, 42.4 mmol), and (3-alanine t-butyl ester hydrochloride (2.1 g, 11.7) 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-6f2bc008926d4aaab76bc05bcbc7de95
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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