Imidazole → HCID 66738448, compound

HRID 558148Notes

Reaction equation

HRID 558148 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:20]I.N1C=CN=C1.O[CH2:28][C:29]1[N:30]=[N:31][N:32]([CH2:34][CH2:35][N:36]2[C:44](=[O:45])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]2=[O:46])[CH:33]=1>C(Cl)Cl>[I:20][CH2:28][C:29]1[N:30]=[N:31][N:32]([CH2:34][CH2:35][N:36]2[C:44](=[O:45])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]2=[O:46])[CH:33]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 62400742HCID 62400742, compound

Product 1

HCID 66738448HCID 66738448, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Stir a mixture of triphenylphosphine (0.29 g, 1.10 mmol) and iodine (0.28 g, 1.10 mmol) in DCM (4 mL) for 10 min. Add 1H-imidazole (0.12 g, 1.84 mmol) and stir for 10 min. Add 2-(2-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)ethyl)isoindoline-1,3-dione (0.2 g, 0.73 mmol) and stir overnight at RT. Dilute with DCM and wash with water and aqueous saturated sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (DCM to 20% ethyl acetate in DCM) to give the title compound as a yellow solid (0.22 g, 78%). MS (ES) m/z 383 [M+1]+.

Workup

  1. washwash with water and aqueous saturated sodium chloride
  2. dry with materialDry over sodium sulfate
  3. concentrationConcentrate the solution in vacuo
  4. customPurify by column chromatography (DCM to 20% ethyl acetate in DCM)

Sources & evidence

ORD record
ord-0383ea10f8a14a569c1b067b5fc06ba9
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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