Potassium Iodide → HCID 70983865, compound

HRID 2171953Notes

Reaction equation

HRID 2171953 reaction equation
[OH-].[K+].[CH:3]1[CH:8]=[C:7]([NH:9][C:10]2[N:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]=[CH:5][CH:4]=1.[I-].[K+].Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>CS(C)=O>[N:15]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:9]([C:7]1[CH:8]=[CH:3][CH:4]=[CH:5][N:6]=1)[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 145472,2'-DipyridylamineHCID 14797Potassium HydroxideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 70983865HCID 70983865, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Tert-butyl 2-(di(pyridine-2-yl)amino)acetate was prepared with modification to Kirin et al., 2007, J. Inorg. Chem., 3686-3694, the entire contents of which are incorporated herein by reference. Potassium hydroxide (3.0 g, 53.6 mmol, 4.6 equiv) was added to a solution of 2,2′-dipyridylamine (2.0 g, 11.7 mmol) in 40 ml DMSO and stirred at room temperature for 16 hours (h). Potassium iodide (200 mg, 1.2 mmol, 0.1 equiv) and tert-butyl bromoacetate (4 ml, 2.3 equiv) were added to the mixture, and the reaction was stirred for 2 h at room temperature. The reaction mixture was extracted with diethyl ether (3×50 ml). The organic fractions were combined and dried over magnesium sulfate, and the solvent was removed by rotary evaporation. The crude product was isolated by flash chromatography (SiO2, hexane/ethyl acetate=8:2) to give a yellow oil. DPA was obtained (Yield: 2.92 g (88%)), and confirmed by 1H NMR (CDCl3, 300 MHz): δ 8.33 (ddd, J=5.0, 1.9, 0.9 Hz; 2H), 7.53 (m, 2H), 7.23 (m, 2H), 6.88 (ddd, J=7.2, 5.0, 0.9 Hz; 2H), 4.84 (s, 2H), 1.42 (s, 9H). ESI-MS (cation): 286 m/z (M+H+) obsd, 286 m/z calcd.

Workup

  1. stirringthe reaction was stirred for 2 h at room temperature
  2. extractionThe reaction mixture was extracted with diethyl ether (3×50 ml)
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-c66dd3c555484f9c969eaccecb44893d
Source dataset
uspto-grants-2015_06
Patent number
US09051345B2

Reaction notes

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