Imidazole → HCID 18394781, compound

HRID 1602633Notes

Reaction equation

HRID 1602633 reaction equation
[CH2:1]([N:8]1[C@H:12]([CH2:13]O)[CH2:11][C@H:10]([CH2:15][CH2:16][C:17]2([CH3:22])[O:21][CH2:20][CH2:19][O:18]2)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:48]I>CC#N>[CH2:1]([N:8]1[C@H:12]([CH2:13][I:48])[CH2:11][C@H:10]([CH2:15][CH2:16][C:17]2([CH3:22])[O:21][CH2:20][CH2:19][O:18]2)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 18394780HCID 18394780, compound

Product 1

HCID 18394781HCID 18394781, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 11-4 (2.0 g, 6.26 mmol), PPh3 (2.63 g, 10.0 mmol), imidazole (725 mg, 10.6 mmol) and CH3CN (30 mL) at 0° C. was added I2 (2.39 g, 9.39 mmol) in five portions over 15 minutes. After 20 minutes, the reaction was warmed to 50° C. for 30 minutes and then poured into 200 mL 1:1 EtOAc/hexanes. The solution was washed with 10% sodium bisulfite, sat NaHCO3, brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 40% EtOAc/hexanes) gave 11-5 as an oil.

Workup

  1. washThe solution was washed with 10% sodium bisulfite
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4b352d30dcd743bf832e07795cf477d8
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

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