Trifluoroacetic acid → Methyl 2-((5-bromopyridin-2-yl)amino)acetate

HRID 1690323Notes

Reaction equation

HRID 1690323 reaction equation
C(O)(C(F)(F)F)=O.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([N:15](C(OC(C)(C)C)=O)[CH2:16][C:17]([O:19][CH3:20])=[O:18])=[N:13][CH:14]=1>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22139000Methyl 2-[(5-bromopyridin-2-yl)[(tert-butoxy)carbonyl]amino]acetate

Product 1

HCID 22139049Methyl 2-((5-bromopyridin-2-yl)amino)acetateYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 50% solution of TFA in CH2Cl2 (200 mL) was added to 5-bromo-[N-(tert-butoxycarbonyl)-N-(methoxycarbonylmethyl)amino]pyridine (16.5 g, 46 mmole). After stirring for 45 min the reaction was concentrated to dryness, and the residue was diluted with 1.0 N Na2CO3 (300 mL). The mixture was extracted with EtOAc (300 mL), and the organic layer was washed with brine, dried (Na2SO4), and concentrated to dryness under vacuum. The title compound (11.32 g, 100%) was obtained as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.13 (d, J=2.3 Hz, 1 H), 7.48 (dd, 1 H), 6.40 (d, J=8.8 Hz, 1 H), 4.95 (br s, 1H), 4.12 (d, J=5.5 Hz, 2 H), 3.78 (s, 3H).

Workup

  1. concentrationwas concentrated to dryness
  2. additionthe residue was diluted with 1.0 N Na2CO3 (300 mL)
  3. extractionThe mixture was extracted with EtOAc (300 mL)
  4. washthe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-be0837d2f9b841fbb1e311d90653a399
Source dataset
uspto-grants-2012_04
Patent number
US08153652B2

Reaction notes

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