Imidazole → HCID 89940958, compound

HRID 1501820Notes

Reaction equation

HRID 1501820 reaction equation
O[CH:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[C:5](=[O:19])[N:4]([C:20]2[CH2:21][O:22][C:23](=[O:25])[CH:24]=2)[CH:3]1[CH3:26].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:51]I>C1(C)C=CC=CC=1>[I:51][CH:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[C:5](=[O:19])[N:4]([C:20]2[CH2:21][O:22][C:23](=[O:25])[CH:24]=2)[CH:3]1[CH3:26]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 86709516HCID 86709516, compound

Product 1

HCID 89940958HCID 89940958, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the compound of step C (370 mg, 1.01 mmol) in toluene (20 mL) at rt was added PPh3 (397 mg, 1.515 mmol), imidazole (137 mg, 2.02 mmol), and I2 (384 mg, 1.515 mmol). The mixture was stirred for 10 h at 100° C., and quenched with NaHCO3 aqueous solution. The organic layer was diluted with DCM, separated, and the aqueous layer was extracted with DCM. The combined organic layers were dried (MgSO4) and purified by column chromatography (0-100% EtOAc/hex) to give the title compound. LC/MS: [(M+1−56)]+=421

Workup

  1. customquenched with NaHCO3 aqueous solution
  2. additionThe organic layer was diluted with DCM
  3. customseparated
  4. extractionthe aqueous layer was extracted with DCM
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. custompurified by column chromatography (0-100% EtOAc/hex)

Sources & evidence

ORD record
ord-f4963525d18c475d953346b1f870f87a
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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