Dichloromethane → HCID 86677548, compound

HRID 2368487Notes

Reaction equation

HRID 2368487 reaction equation
[F:1][C:2]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]([F:19])[C:3]=1[C:4](=[NH:13])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.Br/[C:21](=[CH:24]/OC(C)C)/[CH:22]=[O:23].C(=O)([O-])[O-].[K+].[K+].ClCCl>C(Cl)(Cl)Cl.O>[F:12][C:9]1[CH:10]=[CH:11][C:6]([N:5]2[C:21]([CH:22]=[O:23])=[CH:24][N:13]=[C:4]2[C:3]2[C:14]([F:19])=[CH:15][CH:16]=[C:17]([F:18])[C:2]=2[F:1])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 11106215HCID 11106215, compoundHCID 178512046HCID 178512046, compound

Product 1

HCID 86677548HCID 86677548, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

A mixture of 2,3,6-trifluoro-N-(4-fluorophenyl)benzimidamide (25) (0.98 mg, 3.65 mmol), (E)-2-bromo-3-isopropoxyacrylaldehyde (1.1 g, 5.48 mmol), and potassium carbonate (0.76 g, 5.48 mmol) in chloroform (7 mL) and water (1 mL) was stirred at room temperature overnight. Dichloromethane and water were added and the layers were separated. The aqueous layer was extracted with dichloromethane and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-40% EtOAc in hexanes) to afford 1-(4-fluorophenyl)-2-(2,3,6-trifluorophenyl)-1H-imidazole-5-carbaldehyde (26).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (0-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5e9b334910b149b68698c88ec099ac3d
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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