Imidazole → HCID 20717829, compound

HRID 1250226Notes

Reaction equation

HRID 1250226 reaction equation
[I:1]I.[Cl:3][C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][C:10]2[N:19]([CH2:20][CH2:21][CH2:22]O)[C:18](=[O:24])[C:17]3[C:12](=[C:13]([O:25][CH3:26])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:3][C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][C:10]2[N:19]([CH2:20][CH2:21][CH2:22][I:1])[C:18](=[O:24])[C:17]3[C:12](=[C:13]([O:25][CH3:26])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 18327323HCID 18327323, compound

Product 1

HCID 20717829HCID 20717829, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

Iodine (1016 mg, 4 mmol) was added to a mixture of the product from Step A above, triphenylphosphine (1050 mg, 4 mmol) and imidazole (545 mg, 8 mmol) in toluene (20 mL) at 0° C. The reaction mixture was slowly allowed to warm to room temperature and was stirred for 17 h and diluted with CHCl3. The organic solution was washed with sat'd aq NaHCO3, sat'd aq NaCl, dried and concentrated. The crude residue was chromatographed on SiO2-gel using 30% EtOAc/hexanes to yield the product as a yellow oil (450 mg, 35%). API-MS: 485 (M+1). 1H NMR (300 MHz, CDCl3): d 7.8 (d, 1 H), 7.35 (t, 1 H), 7.2 (d, 2 H), 7.1 (d, 1 H), 6.9 (d, 2 H), 5.15 (s, 2 H), 4.1 (t, 2 H), 3.93 (s, 3 H), 3.9 (s, 3 H), 3.15 (t, 2 H), 2.23 (m, 2 H).

Workup

  1. customat 0° C
  2. washThe organic solution was washed with sat'd aq NaHCO3
  3. customdried
  4. concentrationconcentrated
  5. customThe crude residue was chromatographed on SiO2-gel

Sources & evidence

ORD record
ord-8886bacbaa0d48de958fc6a7c7f16b04
Source dataset
uspto-grants-2002_01
Patent number
US06337332B1

Reaction notes

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