Benzenesulfinic acid, sodium salt → 5-(1,3-Dioxolan-2-yl)-3-(phenylsulfonyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

HRID 1038387Notes

Reaction equation

HRID 1038387 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=[C:9]2I.[C:24]1([S:30]([O-:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Na+]>>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=[C:9]2[S:30]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:32])=[O:31]

Participants

3

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium saltHCID 584076045-(1,3-Dioxolan-2-yl)-3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

Product 1

HCID 584075995-(1,3-Dioxolan-2-yl)-3-(phenylsulfonyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

Procedure

The title compound was prepared following the procedure described for Example 9A using 150 mg (0.336 mmol) 5-(1,3-dioxolan-2-yl)-3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole (Example 6A) and 164 mg (1.01 mmol) sodium benzenesulfinate. After cooling, the reaction mixture was filtered, and the filtrate was purified by preparative RP-HPLC (acetonitrile/water+0.05% TFA gradient) to give 55 mg of a product mixture containing the title compound. This mixture was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. customthe filtrate was purified by preparative RP-HPLC (acetonitrile/water+0.05% TFA gradient)

Sources & evidence

ORD record
ord-b55af68931114250a884a301c3b9a3a7
Source dataset
uspto-grants-2013_10
Patent number
US08551989B2

Reaction notes

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