Cesium carbonate → HCID 28560964, compound

HRID 2205573Notes

Reaction equation

HRID 2205573 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7]C)=[O:6].[CH:12]([C:15]1[NH:16][CH:17]=[CH:18][N:19]=1)([CH3:14])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.[Cu]I>[CH:12]([C:15]1[N:16]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([OH:7])=[O:6])[CH:17]=[CH:18][N:19]=1)([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1234571H-Imidazole, 2-(1-methylethyl)-HCID 38477682-Bromo-isonicotinic acid methyl ester

Product 1

HCID 28560964HCID 28560964, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 2-bromoisonicotinate (2.00 g, 9.26 mmol), 2-isopropyl-1H-imidazole (1.12 g, 10.2 mmol), cesium carbonate (6.03 g, 18.5 mmol) and copper (1) Iodide (176 mg, 926 umol) in DMSO was heated to 120° C. for eighteen hours, under nitrogen. The crude material was filtered, purified by preparative HPLC (10-90% CH3CN in water). The pure fractions were collected and concentrated to give 2-(2-isopropyl-1H-imidazol-1-yl)isonicotinic acid as a white sticky solid (1.176 g, 55% yield). MS 232 (MH+).

Workup

  1. filtrationThe crude material was filtered
  2. custompurified by preparative HPLC (10-90% CH3CN in water)
  3. customThe pure fractions were collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f0ac8e89778a4f86b2bfff85374e9a74
Source dataset
uspto-grants-2016_06
Patent number
US09371317B2

Reaction notes

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