Sodium Iodide → 4-(6,7-dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-2-iodo-phenol

HRID 2251123Notes

Reaction equation

[N:1]1[N:12]2[C:4]([N:5]=[C:6]3[C:10](=[C:11]2[C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8][CH2:7]3)=[CH:3][CH:2]=1.[Na+].[I-:21].[OH-].[Na+].[O-]Cl.[Na+]>CO>[N:1]1[N:12]2[C:4]([N:5]=[C:6]3[C:10](=[C:11]2[C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([I:21])[CH:14]=2)[CH2:9][CH2:8][CH2:7]3)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-(6,7-Dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-phenol (500 mg, 0.002 mmol) was dissolved in methanol (10 mL) followed by addition of NaI (368 mg, 2.45 mmol) and NaOH (98 mg, 2.45 mmol). The solution was cooled to 0° C. followed by dropwise addition of NaOCl (5.25% aq, 3.8 ml) over 3 minutes. The reaction mixture was stirred at 0° C. for 1 hour followed by warming to room temperature and quenching with sodium thiosulphate (saturated. aq., 6 ml). The pH of the reaction was adjusted to ˜7 by addition of sodium dihydrogen phosphate. The solution was extracted with CH2Cl2. The organic layer was dried and concentrated. The residue was purified on silica gel (10%→60% EtOAc in hexane) to give 4-(6,7-dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-2-iodo-phenol.

Workup

temperatureby warming to room temperature
customquenching with sodium thiosulphate (saturated. aq., 6 ml)
additionThe pH of the reaction was adjusted to ˜7 by addition of sodium dihydrogen phosphate
extractionThe solution was extracted with CH2Cl2
customThe organic layer was dried
concentrationconcentrated
customThe residue was purified on silica gel (10%→60% EtOAc in hexane)

Sources & evidence

ORD record: ord-39327a82a1a64bd882b580c972bcd673
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319103B2

Reaction notes

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