Water → (2-Amino-5-bromo-pyridin-3-ylmethoxy)-acetic acid ethyl ester

HRID 712627Notes

Reaction equation

HRID 712627 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH2:5][OH:6])[CH3:2].[H-].[Na+].Br.[Br:11][C:12]1[CH:13]=[C:14]([CH2:19]Br)[C:15]([NH2:18])=[N:16][CH:17]=1.O>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:7])[CH2:5][O:6][CH2:19][C:14]1[C:15]([NH2:18])=[N:16][CH:17]=[C:12]([Br:11])[CH:13]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

Product 1

HCID 57742064(2-Amino-5-bromo-pyridin-3-ylmethoxy)-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Hydroxy acetic acid ethyl ester (294 mg, 2.8 mmol) is dissolved in 5.0 mL of DMF and 60% sodium hydride (113 mg, 2.8 mmol) is added at 0° C. The mixture is stirred for 15 min and 5-bromo-3-bromomethyl-pyridin-2-ylamine hydrobromide (392 mg, 1.1 mmol) is added. The mixture is warmed up to room temperature for 2.5 hr. Then water (15 mL) is added along with EtOAc (30 mL). The mixture is stirred for 10 min and the aqueous layer is separated and extracted with EtOAc (2×20 mL). The organic layers are combined and concentrated to give (2-amino-5-bromo-pyridin-3-ylmethoxy)-acetic acid ethyl ester.

Workup

  1. stirringThe mixture is stirred for 10 min
  2. customthe aqueous layer is separated
  3. extractionextracted with EtOAc (2×20 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-59c0220dc15e4c5791743a7be7b973ce
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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