Water → HCID 86691623, compound

HRID 624312Notes

Reaction equation

HRID 624312 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]3[NH:18][CH2:19][CH2:20][N:21]=3)[C:6]=2[C:22]=1[F:23].C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]3[NH:21][CH:20]=[CH:19][N:18]=3)[C:6]=2[C:22]=1[F:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12217721Iodo benzene diacetateHCID 86691622HCID 86691622, compound

Product 1

HCID 86691623HCID 86691623, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of 2-(5-chloro-4-fluoro-2-(4-fluorophenyl)benzofuran-3-yl)-4,5-dihydro-1H-imidazole (0.65 g, 1.954 mmol) in DMSO (5 ml) in a 25 ml RB flask was added potassium carbonate (0.405 g, 2.93 mmol) and iodobenzene diacetate (0.755 g, 2.344 mmol). The reaction mixture was stirred at room temperature in darkness overnight. The reaction mixture was added water and extracted with ethyl acetate (3×25 ml). The combined organic extracts were dried over Na2SO4, filtered and concentrated. The crude product was purified by using 40 g combiflash silica column with 11% methanol in chloroform as an eluent. The desired fractions were collected and concentrated to give the titled product (0.25 g, 39%). 1H NMR (400 MHz, CDCl3): δ 9.45 (s, 1H), 7.92-7.89 (m, 2H), 7.36-7.30 (m, 2H), 7.26-7.21 (m, 2H), 7.11-7.07 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (3×25 ml)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified
  6. customThe desired fractions were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4a8a6af8205449ef83d66fc40c2a183a
Source dataset
uspto-grants-2016_04
Patent number
US09303020B2

Reaction notes

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