Potassium Iodide → 5-iodo-3-(pyridin-4-yl)-1-trityl-1H-indazole

HRID 1465710Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13](N)[CH:14]=3)[N:9]([C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:8]=2)=[CH:3][CH:2]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.N([O-])=O.[Na+].[I-:52].[K+]>CC#N.O.CCOC(C)=O>[I:52][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[N:8]=[C:7]2[C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 10 °C

Procedure

To the stirred solution of 3-(pyridin-4-yl)-1-trityl-1H-indazol-5-amine (6.02 g, 13.3 mmol) in MeCN (45 mL) was added p-toluenesulfonic acid monohydrate (3.37 g, 17.7 mmol). After cooled to 10° C., a solution of sodium nitrite (1.84 g, 26.6 mmol), potassium iodide (5.52 g, 33.2 mmol) in water (9 mL) was added dropwise. The resulting dark brown solution was stirred at room temperature for 4 hours. The mixture was diluted with EtOAc and washed with water and 1N Na2S2O3. After dried and concentrated, the crude mixture was column purified with mixture of hexane and EtOAc to give 5-iodo-3-(pyridin-4-yl)-1-trityl-1H-indazole (3.95 g).

Workup

washwashed with water and 1N Na2S2O3
customAfter dried
concentrationconcentrated
custompurified with mixture of hexane and EtOAc

Sources & evidence

ORD record: ord-e4e2be7ff0674c6ba50b6888be8c6902
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999966B2

Reaction notes

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