Iodine → HCID 68328821, compound

HRID 634243Notes

Reaction equation

HRID 634243 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[O:14][C:13]([NH:15][CH:16]([CH3:18])[CH3:17])=[N:12][N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[I:21]I>CN(C=O)C>[I:21][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]3[O:14][C:13]([NH:15][CH:16]([CH3:18])[CH3:17])=[N:12][N:11]=3)[CH:5]=2)[NH:1][CH:2]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 68327956HCID 68327956, compound

Product 1

HCID 68328821HCID 68328821, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (150 mg, 0.6148 mmol) in DMF (1.5 mL) was added 1.2M aq. KOH (1.5 mL) and the reaction was stirred at 0° C. for 5 min. I2 (234 mg, 0.9297 mmol) was added and the mixture was stirred for additional 1 h. The reaction was quenched with H2O (10 mL) to get a pink precipitate. The precipitate was filtered, washed with H2O (6 mL) and dried. The crude product was purified with silica-gel column chromatography (eluent: 50% EtOAc in petroleum ether) to give 5-(3-iodo-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (140 mg, 61%) as a pink solid. MS (ESI, pos. ion) m/z: 369.1 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 11.85 (brs, 1H), 7.68 (m, 2H), 7.65 (m, 1H), 7.62 (d, J=7.2 Hz, 1H), 7.55 (d, J=8.4 Hz, 1H), 3.70-3.75 (m, 1H), 1.20 (d, J=6.4 Hz, 6H).

Workup

  1. stirringthe mixture was stirred for additional 1 h
  2. customThe reaction was quenched with H2O (10 mL)
  3. customto get a pink precipitate
  4. filtrationThe precipitate was filtered
  5. washwashed with H2O (6 mL)
  6. customdried
  7. customThe crude product was purified with silica-gel column chromatography (eluent: 50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-b82a5f2d55cd48b6802ce256e76c18ba
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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