Ethyl bromopyruvate → Ethyl 6-chloro-5-[(diethoxyphosphinyl)methyl]imidazo[1,2-a]pyridine-2-carboxylate

HRID 861992Notes

Reaction equation

HRID 861992 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])[C:5]([Cl:17])=[CH:4][CH:3]=1.Br[CH2:19][C:20](=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>COCCOC.CCO>[Cl:17][C:5]1[CH:4]=[CH:3][C:2]2[N:7]([CH:19]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:1]=2)[C:6]=1[CH2:8][P:9]([O:13][CH2:14][CH3:15])([O:10][CH2:11][CH3:12])=[O:16]

Participants

5

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 86752043Diethyl [(6-amino-3-chloro-2-pyridinyl)methyl]phosphonate

Product 1

HCID 19701397Ethyl 6-chloro-5-[(diethoxyphosphinyl)methyl]imidazo[1,2-a]pyridine-2-carboxylateYield 13%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Following the procedure for Example 17, the residue from Example 28 was combined with ethyl bromopyruvate (0.468 g, 2.4 mmol) in DME (25 mL). After the resulting salt was refluxed in abs EtOH (30 mL) for 6 h, workup and puricication produced 0./114 g (13% of title compound).

Workup

  1. customworkup and puricication produced 0

Sources & evidence

ORD record
ord-277790dcd3c24a0ba46626ad1f117d97
Source dataset
uspto-grants-1998_02
Patent number
US05716964

Reaction notes

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