Iodine → HCID 178477831, compound

HRID 338489Notes

Reaction equation

HRID 338489 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1.[I:23]I.[OH-].[K+].[Cl-].[NH4+]>C(OCC)(=O)C.CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([I:23])=[N:7][NH:8]2)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 807Iodine2×HCID 14797Potassium Hydroxide2×HCID 25517Ammonium ChlorideHCID 89837043HCID 89837043, compound

Product 1

HCID 178477831HCID 178477831, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-chloro-5-[4-(morpholin-4-yl)phenyl]-1H-indazole (72 mg, 0.23 mmol) and N,N-dimethylformamide (3 mL) was treated with iodine (91 mg, 0.36 mmol) and freshly ground potassium hydroxide (16 mg, 0.26 mmol). The reaction mixture was stirred at room temperature for three hours, then treated with additional iodine (50 mg) and potassium hydroxide (20 mg) and heated to 40° C. for 20 minutes. The reaction mixture was poured into ethyl acetate and saturated aqueous ammonium chloride. The layers were separated and the organic phase was washed with 2N sodium thiosulfate. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography utilizing heptanes/ethyl acetate (100:0 to 0:70) to give the title compound (86.7 mg). MS (ES−): 438.0 (M−H)−.

Workup

  1. temperatureheated to 40° C. for 20 minutes
  2. customThe layers were separated
  3. washthe organic phase was washed with 2N sodium thiosulfate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-52bba561d6d349a487d32b21cc6943b4
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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