Iodine → HCID 67959733, compound

HRID 1529380Notes

Reaction equation

HRID 1529380 reaction equation
[I:1]I.[OH-].[K+].[CH:5]1([C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[NH:19][CH:18]=[CH:17]4)[CH:11]=[N:10][CH:9]=2)[CH2:7][CH2:6]1.OS([O-])=O.[Na+]>CN(C=O)C>[CH:5]1([C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[NH:19][CH:18]=[C:17]4[I:1])[CH:11]=[N:10][CH:9]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 23665763Sodium BisulfiteHCID 67960065HCID 67960065, compound

Product 1

HCID 67959733HCID 67959733, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

I2 (1.62 g, 6.38 mmol) followed by powdered KOH (0.671 g, 11.95 mmol) was added to a solution of 5-(6-cyclopropylpyrazin-2-yl)-1H-indole (750 mg, 3.19 mmol) in 7 mL of DMF at RT overnight. The mixture was added to 30 mL of 10% NaHSO3 (aq.). The mixture was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude was purified by silica gel chromatography, eluting with a gradient of 0-30% EtOAc in hexanes, to provide 5-(6-cyclopropylpyrazin-2-yl)-3-iodo-1H-indole (280 mg, 0.78 mmol, 24% yield) as an orange solid. MS (ESI, pos. ion) m/z: 362.0 (M+1).

Workup

  1. extractionThe mixture was extracted with EtOAc (3×)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified by silica gel chromatography
  6. washeluting with a gradient of 0-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-0617613dfb5b455a8418c58576cc5719
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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