2-Amino-5-fluoropyridine → HCID 86666548, compound

HRID 2178554Notes

Reaction equation

HRID 2178554 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[Br:9][CH:10]([CH3:18])[C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13]>COCCOC>[Br-:9].[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N+:3]=1[CH:10]([C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:18]

Participants

4

Reactant 2

HCID 27377012-Amino-5-fluoropyridineHCID 11117285Ethyl 3-bromo-2-oxobutanoate

Product 1

HCID 86666548HCID 86666548, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution 2-amino-5-fluoropyridine (5-A, 3.04 g, 27.1 mmol) and ethyl 3-bromo-2-oxobutanoate (5-B, 5.67 g, 27.1 mmol) in DME (15 mL) was stirred at rt for 1 day. The resultant solid precipitate was collected by filtration, and washed with Et2O, to afford compound 5-C as an off-white solid (5.35 g, 82%), which was used without purification in the subsequent step.

Workup

  1. filtrationThe resultant solid precipitate was collected by filtration
  2. washwashed with Et2O

Sources & evidence

ORD record
ord-65330e4facb44f6984cf18b5ce5401d2
Source dataset
uspto-grants-2015_06
Patent number
US09067935B2

Reaction notes

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