Water → HCID 66885880, compound

HRID 1782058Notes

Reaction equation

HRID 1782058 reaction equation
Br[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[C:6]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[N:5][C:4]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24].[CH:28]([N:31]([CH:34]([CH3:36])C)CC)([CH3:30])C.N1CCCC1.O>C(#N)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([N:7]2[C:3]([CH2:2][N:31]3[CH2:28][CH2:30][CH2:36][CH2:34]3)=[C:4]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:5]=[C:6]2[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 11213962HCID 11213962, compound

Product 1

HCID 66885880HCID 66885880, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part B: To a magnetically stirred solution of ethyl 5-bromomethyl-1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-1H-imidazole-4-carboxylate (11.69 g, 23.9 mmol) in acetonitrile (40 ml) is added diisopropylethylamine (DIPEA) (5.2 ml, 30 mmol) and pyrrolidine (1.7 g, 23.9 mmol) and the resulting solution is reacted at room temperature for 2 hours. Water (250 ml) is added and the resulting mixture is extracted three times with dichloromethane. The collected dichloromethane layers are dried over Na2SO4, filtered and concentrated in vacuo. Subsequent purification with flash chromatography (petroleum ether/EtOAc=20/80 (v/v)) gives ethyl 1-(4-chlorophenyl)-2-(2,4-dichloro-phenyl)-5-(pyrrolidin-1-ylmethyl)-1H-imidazole-4-carboxylate (3.7 gram, 32% yield). 1H-NMR (200 MHz, CDCl3): δ 1.42 (t, J=7 Hz, 3H), 1.62-1.72 (m, 4H), 2.42-2.50 (m, 4H), 3.83 (s, 2H), 4.43 (q, J=7 Hz, 2H), 7.17-7.40 (m, 7H).

Workup

  1. customthe resulting solution is reacted at room temperature for 2 hours
  2. extractionthe resulting mixture is extracted three times with dichloromethane
  3. dry with materialThe collected dichloromethane layers are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customSubsequent purification with flash chromatography (petroleum ether/EtOAc=20/80 (v/v))

Sources & evidence

ORD record
ord-727062505c4d47119f0152126045a718
Source dataset
uspto-grants-2009_03
Patent number
US07498348B2

Reaction notes

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