Sulfuric Acid → 5-azido-3-(pyridin-4-yl)-1-trityl-1H-indazole

HRID 1465685Notes

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]([NH2:16])[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.OS(O)(=O)=O.N([O-])=O.[Na+].[N-:45]=[N+:46]=[N-].[Na+]>O>[N:16]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:17]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[N:8]=[C:7]2[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)=[N+:45]=[N-:46]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 1 L round bottom flask equipped with a magnetic stir bar was suspended 3-(pyridin-4-yl)-1-trityl-1H-indazol-5-amine (13.00 g, 28.7 mmol) in 400.00 ml of water and cooled to 0° C. 80 ml of cone. H2SO4 was added slowly over a period of 15 min at 0° C. A solution of NaNO2(2.48 g, 35.9 mmol) in 15 ml of water was added to the mixture and allowed to stir at 0° C. for 30 min. A solution of NaN3 (3.36 g, 51.7 mmol) in water was then added dropwise over a period of 15 min. The mixture was slowly warmed to room temperature and stirred overnight. Upon completion, the precipitate was filtered, washed with water and dried to give 5-azido-3-(pyridin-4-yl)-1-trityl-1H-indazole (12.62 g) as a yellow solid.

Workup

customTo a 1 L round bottom flask equipped with a magnetic stir bar
temperatureThe mixture was slowly warmed to room temperature
stirringstirred overnight
filtrationUpon completion, the precipitate was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-a5da4d78414e49bdbb68f603f9e90d3a
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999966B2

Reaction notes

Loading…