Acetic Acid → HCID 86677552, compound

HRID 2368496Notes

Reaction equation

HRID 2368496 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[NH:23])[C:10]([CH3:22])([CH3:21])[CH2:11][C:12]2[C:17]([F:18])=[CH:16][CH:15]=[C:14]([F:19])[C:13]=2[F:20])=[CH:4][CH:3]=1.C(O)(=O)C.C(N(CC)CC)C.Br[CH:36]([CH:39]=O)[CH:37]=[O:38]>C(O)(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:36]([CH:37]=[O:38])=[CH:39][N:23]=[C:9]2[C:10]([CH3:21])([CH3:22])[CH2:11][C:12]2[C:17]([F:18])=[CH:16][CH:15]=[C:14]([F:19])[C:13]=2[F:20])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 749452-BromopropanedialHCID 178441226HCID 178441226, compound

Product 1

HCID 86677552HCID 86677552, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of N-(4-fluorophenyl)-2,2-dimethyl-3-(2,3,6-trifluorophenyl) propanimidamide (35) (72.8 mg, 0.22 mmol), acetic acid (14 μL, 0.24 mmol), triethylamine (33 μL, 0.24 mmol), and bromomalonaldehyde (33.9 mg, 0.22 mmol) in isopropyl alcohol (1 mL) was refluxed for 4 h. The reaction was concentrated in vacuo, dichloromethane was added and washed with water. The aqueous phase 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 (0-30% EtOAc in hexanes) to afford 1-(4-fluorophenyl)-2-(2-methyl-1-(2,3,6-trifluorophenyl)propan-2-yl)-1H-imidazole-5-carbaldehyde (36).

Workup

  1. concentrationThe reaction was concentrated in vacuo, dichloromethane
  2. additionwas added
  3. washwashed with water
  4. extractionThe aqueous phase was extracted with dichloromethane
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-60e1a594e50c4a459a06eb2587d45398
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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