Methanol → 5-bromo-3-methyl-1-(toluene-4-sulfonyl)-1H-indazol-6-ylamine

HRID 1691806Notes

Reaction equation

[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[N:4]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[N:3]=1.CO.[Br-:24].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>ClCCCl>[Br:24][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[NH2:11])[N:4]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[N:3]=[C:2]2[CH3:1]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Methyl-1-(toluene-4-sulfonyl)-1H-indazol-6-ylamine (301 mg, 1.0 mmol) was dissolved in 1,2-dichloroethane (80 ml) and methanol (40 ml) at room temperature. The mixture was heated to 80° C. and then the tetrabutylammonium tribromide (1.0 eq, 482 mg) was added. Stirring was continued for 10 minutes, and then the mixture was partitioned between diethyl ether and saturated aqueous sodium sulfite solution. The organic layer was separated, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (gradient 9:1 to 4:1 hexanes/ethyl acetate) to give 5-bromo-3-methyl-1-(toluene-4-sulfonyl)-1H-indazol-6-ylamine (280 mg, 73.7%) as a white powder.

Workup

customat room temperature
customthe mixture was partitioned between diethyl ether and saturated aqueous sodium sulfite solution
customThe organic layer was separated
washwashed with water
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (gradient 9:1 to 4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-913038bc785744b7840714c7b888a72d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153809B2

Reaction notes

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