Water → HCID 58204877, compound

HRID 886011Notes

Reaction equation

HRID 886011 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH2:7][O:8][C:9]1[C:10](I)=[N:11][CH:12]=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15].C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.[Cu-]=O>[N:11]1[C:10]2[N:3]3[CH:4]=[CH:5][N:1]=[C:2]3[CH2:6][CH2:7][O:8][C:9]=2[CH:18]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10236NinhydrinHCID 11430Potassium CarbonateHCID 58204813methyl 5-(2-(1H-imidazol-2-yl)ethoxy)-6-iodonicotinate

Product 1

HCID 58204877HCID 58204877, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of methyl 5-(2-(1H-imidazol-2-yl)ethoxy)-6-iodonicotinate (373 mg, 1.00 mmol), Copper(I) oxide (14.3 mg, 0.10 mmol), Ninhydrin (35.6 mg, 0.20 mmol) and potassium carbonate (290 mg, 2.10 mmol) in dimethyl sulfoxide (10.0 mL) was heated at 110° C. for 2 hours. The mixture was poured into 20 ml of water and extracted with ethyl acetate (3×15 ml). The organic extracts were washed with water (3×15 ml), brine, dried over MgSO4 and concentrated. The residue (0.220 g, 90%) was used without further purification in the next step. MS (ESI+): 246.0. 1H NMR (500 MHz, CDCl3) δ 8.77 (d, J=1.9, 1H), 8.10 (s, 1H), 8.04 (d, J=1.9, 1H), 7.08 (s, 1H), 4.47 (t, J=5.1, 2H), 3.97 (s, 3H), 3.46 (t, J=5.1, 2H).

Workup

  1. extractionextracted with ethyl acetate (3×15 ml)
  2. washThe organic extracts were washed with water (3×15 ml), brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue (0.220 g, 90%) was used without further purification in the next step

Sources & evidence

ORD record
ord-0b636352096c44d7b1609ae3a27da0ab
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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