Iodine → HCID 72721600, compound

HRID 626985Notes

Reaction equation

HRID 626985 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]([C:11]1[N:15]2[CH:16]=[C:17]([C:20]3[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=3)[CH:18]=[CH:19][C:14]2=[N:13][C:12]=1[CH3:26])O.II>C(O)(=O)C.[PH2](=O)O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][C:11]1[N:15]2[CH:16]=[C:17]([C:20]3[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=3)[CH:18]=[CH:19][C:14]2=[N:13][C:12]=1[CH3:26]

Participants

5

Reactant 2

HCID 807Iodine2×HCID 72721705HCID 72721705, compound

Product 1

HCID 72721600HCID 72721600, compoundYield 26.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 4124402Phosphinic AcidSolvent2×

Procedure

To a suspension of Example 8 (0.10 g) in a mixture of acetic acid (2 mL) and phosphinic acid (0.1 mL) was added iodine (0.05 g). The mixture was heated at 100° C. for 1.5 h before the addition of extra iodine (8 mg) and phosphinic acid (0.02 mL). Heating was continued for 4 h and then the mixture was cooled to room temperature overnight. The mixture was concentrated in vacuo and the residue was partitioned between DCM (20 mL) and saturated aqueous NaHCO3 solution (20 mL). The organic phase was separated, dried (Na2SO4), filtered and concentrated in vacuo. The resulting crude product was purified by preparative HPLC to give the title compound (0.025 g) as a white solid. δH (400 MHz, DMSO-d6) 7.21 (t, 1H, J 1.2 Hz), 6.95 (s, 1H), 6.78 (d, 1H, J 0.6 Hz), 6.55 (m, 2H), 6.46 (d, 1H, J 8.5 Hz), 6.27 (dd, 1H, J 8.5, 2.5 Hz), 5.93 (d, 1H, J 2.5 Hz), 3.45 (s, 2H), 2.91 (s, 3H), 1.36 (s, 3H). MH+ 372.

Workup

  1. temperatureHeating
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between DCM (20 mL) and saturated aqueous NaHCO3 solution (20 mL)
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-cea96fdfffaa442fa82586fc8517bcef
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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