Bromine → HCID 86711541, compound

HRID 512498Notes

Reaction equation

HRID 512498 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[CH:13]=[CH:12][C:11](=[O:14])[C:10]([C:15]([OH:17])=[O:16])=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].[Br:20]Br>C(O)(=O)C>[Br:20][C:12]1[C:11](=[O:14])[C:10]([C:15]([OH:17])=[O:16])=[CH:9][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:19][CH:18]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 86711539HCID 86711539, compound

Product 1

HCID 86711541HCID 86711541, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-(4-cyano-benzyl)-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 12a, 2.57 g, 10.1 mmol) in glacial acetic acid (10 ml) is added bromine (2 mL). The reaction mixture is stirred for 6 days at room temperature and additional bromine (1 mL) is added on the first 2 days, respectively. The reaction mixture is evaporated under reduced pressure and co-evaporated with toluene twice. The remaining residue is purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.). Yield: 566 mg (17% of theory); ESI mass spectrum: [M+H]+=333 (bromine isotope pattern); Retention time HPLC: 0.84 min (Z002—002).

Workup

  1. customThe reaction mixture is evaporated under reduced pressure and co-evaporated with toluene twice
  2. customThe remaining residue is purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.)
  3. custom0.84 min (Z002—002)

Sources & evidence

ORD record
ord-c26a46f21818439aa7575c3c29b13464
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Reaction notes

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