Iodine → HCID 178506565, compound

HRID 1529373Notes

Reaction equation

HRID 1529373 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][N: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][N: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 679600815-(6-cyclopropylpyrazin-2-yl)-1H-indazole

Product 1

HCID 178506565HCID 178506565, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

I2 (269 mg, 1.06 mmol) followed by powdered KOH (111 mg, 1.98 mmol) was added to a solution of 5-(6-cyclopropylpyrazin-2-yl)-1H-indazole (125 mg, 0.53 mmol) in 1 mL of DMF at RT overnight. The mixture was added to 5 mL of 10% NaHSO3 (aq.). The mixture was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give 5-(6-cyclopropylpyrazin-2-yl)-3-iodo-1H-indazole (192 mg, 0.53 mmol, 100% yield) as an orange solid. MS (ESI, pos. ion) m/z: 362.9 (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

Sources & evidence

ORD record
ord-4f25c64409d9451eafc4a7bd9ea6802a
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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