Iodine chloride → 4-(2-Fluoro-4-iodophenylamino)-1-(toluene-4-sulfonyl)-1H-indazole-5-carboxylic acid methyl ester

HRID 79016Notes

Reaction equation

HRID 79016 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Si](C)(C)C)=[CH:27][C:26]=2[F:35])=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[N:9]=[CH:8]2)=[O:4].[I:36]Cl>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:6]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([I:36])=[CH:27][C:26]=2[F:35])=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[N:9]=[CH:8]2)=[O:4]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 670839874-(2-Fluoro-4-trimethylsilanylphenylamino)-1-(toluene-4-sulfonyl)-1H-indazole-5-carboxylic acid methyl ester

Product 1

HCID 670840904-(2-Fluoro-4-iodophenylamino)-1-(toluene-4-sulfonyl)-1H-indazole-5-carboxylic acid methyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(2-fluoro-4-trimethylsilanylphenylamino)-1-(toluene-4-sulfonyl)-1H-indazole-5-carboxylic acid methyl ester (0.56 g, 1.1 mmol) in DCM (3 mL) at 0° C. was added a solution of iodine monochloride in DCM (2.2 mL, 1M, 2.2 mmol). The reaction mixture was stirred at 0° C. for 30 minutes. The reaction was quenched by the addition of water (10 mL) then diluted with saturated aqueous sodium thiosulfate solution (10 mL). The resultant mixture was extracted with ethyl acetate (3×20 mL) and the combined organic fractions washed with brine (20 mL), dried (MgSO4) then concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0-100% DCM in cyclohexane) to yield the title compound as a light brown solid (0.51 g, 83%). LCMS (Method B): RT=4.87 min, [M+H]+=566.

Workup

  1. customThe reaction was quenched by the addition of water (10 mL)
  2. additionthen diluted with saturated aqueous sodium thiosulfate solution (10 mL)
  3. extractionThe resultant mixture was extracted with ethyl acetate (3×20 mL)
  4. washthe combined organic fractions washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-4246e28526fd4a2daa3987a8eb8ce992
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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