Sodium Carbonate → Methyl 3-iodoimidazo[1,2-a]pyridine-7-carboxylate

HRID 341242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341242
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][C:5]=12.[I:14]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[I:14][C:3]1[N:4]2[CH:9]=[CH:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][C:5]2=[N:1][CH:2]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 15096964Methyl imidazo(1,2-a)pyridine-7-carboxylate

Produkt 1

HCID 57497695Methyl 3-iodoimidazo[1,2-a]pyridine-7-carboxylateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of Methyl imidazo[1,2-a]pyridine-7-carboxylate (3.8 g, 21.6 mmol, 1.0 equiv) in DMF (20 ml) was added N-iodosuccinimide (5.8 g, 26 mmol, 1.2 equiv) and the resulting mixture was stirred for 2 h at room temperature. The brown slurry was diluted with water, 10% w/v sodium thiosulfate and sodium carbonate (1M) and the resulting white solid was removed by filtration, washed with ether and dried to afford 4.7 g of product. MS: [M+H]+ 303; 1H NMR (400 MHz, Me-d3-OD): 8.44 (1H, d), 8.25 (1H, s), 7.88 (1H, s), 7.61 (1H, dd), 3.95 (3H, s).

Aufarbeitung

  1. customthe resulting white solid was removed by filtration
  2. washwashed with ether
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f3416b15655e4452a21d2425dfb85e13
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895745B2

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