Iodine → HCID 178515460, compound

HRID 2215763Notes

Reaction equation

HRID 2215763 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]2[C:11](=O)[NH:12][C:13](=[O:24])[C:14]=2[C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH:3]=[CH:2]1.II.[O:28]1CCOCC1>>[CH:3]1[CH:2]=[N:1][C:9]2[C:4]=1[CH2:5][CH:6]=[C:7]1[C:16]3[C:15]([C:23]4[CH2:22][C:21](=[O:28])[CH:20]=[CH:19][C:18]=4[N:17]=3)=[C:14]3[C:13](=[O:24])[NH:12][CH:11]=[C:10]3[C:8]=21

Participants

4

Reactant 3

HCID 807IodineHCID 312751,4-DioxaneHCID 21950002HCID 21950002, compound

Product 1

HCID 178515460HCID 178515460, compound

Procedure

A solution of 3-(1H-indol-7-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione (140 mg, 0.428 mmol) and iodine (114 mg, 0.449 mmol) in dioxane (200 mL) was photolyzed with a 450 W Hanovia lamp fitted with pyrex filter for 20 minutes. The mixture was concentrated to ˜20 mL, poured into EtOAc and washed with 10% aq NaHSO3, water (3×), saturated aq NaHCO3, and brine, dried (MgSO4), filtered and concentrated onto SiO2. Flash Chromatography (30% EtOAc/hexanes) afforded the title compound as an orange powder which was dried under vacuum at 70° C. for overnight (66 mg, 47%). 1H NMR (400 MHz, DMSO-d6) 12.78 (s, 1H), 12.62 (s, 1H), 11.51 (S, 1H), 8.96 (d, J=8 Hz, 1H), 8.31 (d, J=8 Hz, 1H), 8.10 (d, J=8 Hz, 1H), 7.70–7.76 (m, 2H), 7.56 (dd, J=8, 8 Hz, 1H), 7.38 (dd, J=8, 8 Hz, 1H), 6.81 (br s, 1H). MS (electrospray, m/z) 326 (M++1), 324 (M−−1) 324. HRMS 326.0941 (M++1, calcd for C20H12N3O2 326.0930).

Workup

  1. customfitted with pyrex
  2. filtrationfilter for 20 minutes
  3. concentrationThe mixture was concentrated to ˜20 mL
  4. additionpoured into EtOAc
  5. washwashed with 10% aq NaHSO3, water (3×), saturated aq NaHCO3, and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated onto SiO2

Sources & evidence

ORD record
ord-bc8fe5c4f3414b9293d3c99dc9482cf9
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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