Diisopropylethylamine → 1-[(6-Bromopyridin-2-yl)methyl]-4-methyl-1,4-azaphosphinane 4-oxide

HRID 386036Notes

Reaction equation

HRID 386036 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[N:3]=1.Cl.[CH3:11][P:12]1(=[O:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]([CH2:8][N:15]2[CH2:16][CH2:17][P:12](=[O:18])([CH3:11])[CH2:13][CH2:14]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 129547962-Bromo-6-(bromomethyl)pyridineHCID 668330534-Methyl-1,4lambda5-azaphosphinan-4-one hydrochloride

Product 1

HCID 595256551-[(6-Bromopyridin-2-yl)methyl]-4-methyl-1,4-azaphosphinane 4-oxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (500 mg, 1.99 mmol), 4-methyl-1,4-azaphosphinane 4-oxide hydrochloride (406 mg, 2.39 mmol, prepared according to the method described in WO 2008/010985), and DIEA (522 μL, 2.99 mmol) were combined in DMF (5.0 mL) and stirred at room temperature overnight. The solvent was then evaporated in vacuo and the crude residue was purified by reverse phase HPLC (MeCN/water w/0.025% TFA) to afford the title compound as a colorless foam.

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customthe crude residue was purified by reverse phase HPLC (MeCN/water w/0.025% TFA)

Sources & evidence

ORD record
ord-49627ba2896446df9858ad963bc822cb
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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