Imidazole → HCID 67233655, compound

HRID 2280319Notes

Reaction equation

HRID 2280319 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:21])[CH2:10][CH2:11][C:12](=[O:20])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[CH:6][C:7]=1F.[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.N1C=CC=CC=1>CS(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:21])[CH2:10][CH2:11][C:12](=[O:20])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[CH:6][C:7]=1[N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 1049PyridineHCID 58305669HCID 58305669, compound

Product 1

HCID 67233655HCID 67233655, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Ethyl 7-(3,4-difluorophenyl)-4,7-dioxoheptanoate (351 mg) was treated with imidazole (241 mg) and pyridine (395 mg) in DMSO (3 mL) at 150° C. over 7 h with a micro-wave heating. The resultant mixture was diluted with water (12 mL) and was extracted with EtOAc (20 mL×3). After removal the solvents, the mixture was purified by flash silica gel chromatography, eluting with EtOAc, to afford the desired product -ethyl 7-(3-fluoro-4-(1H-imidazol-1-yl)phenyl)-4,7-dioxoheptanoate (279 mg, 68%) as light brown solids.

Workup

  1. extractionwas extracted with EtOAc (20 mL×3)
  2. customAfter removal the solvents
  3. customthe mixture was purified by flash silica gel chromatography
  4. washeluting with EtOAc

Sources & evidence

ORD record
ord-6a107f32b6184ea189eed99190e69860
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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