4-Toluenesulfonyl chloride → 6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-amine

HRID 1695736Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([NH2:13])[C:7]2[CH:8]=[N:9][NH:10][C:11]=2[CH:12]=1.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([NH2:13])[C:7]2[CH:8]=[N:9][N:10]([S:21]([C:18]3[CH:19]=[CH:20][C:15]([CH3:14])=[CH:16][CH:17]=3)(=[O:23])=[O:22])[C:11]=2[CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of sodium hydride (5.66 g) in anhydrous DMF (75 ml) stirring at 0° C. was added a solution of 6-bromo-1H-indazol-4-amine (30 g), also in anhydrous DMF (125 ml), dropwise. The reaction mixture was stirred for 1 h at 0° C. then a solution of 4-methylbenzenesulfonyl chloride (27 g) in anhydrous DMF (100 ml) was added dropwise. The reaction was stirred for 2 h. A further portion of sodium hydride (0.57 g) was added followed by 4-methylbenzenesulfonyl chloride (2.70 g). The reaction mixture was left to stand overnight at room temperature, before pouring onto ice/water (1800 ml). A precipitate formed that was collected by filtration, tritrurated using diethyl ether:methanol (1:1, v/v), then re-collected by filtration and dried in vacuo at 40° C. over the weekend to give title compound, (26.5 g).

Workup

stirringThe reaction mixture was stirred for 1 h at 0° C.
stirringThe reaction was stirred for 2 h
waitThe reaction mixture was left
additionbefore pouring onto ice/water (1800 ml)
customA precipitate formed
filtrationthat was collected by filtration
filtrationv/v), then re-collected by filtration
customdried in vacuo at 40° C. over the weekend

Sources & evidence

ORD record: ord-70d3597a41f54a258877d0a2f807cb61
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163743B2

Reaction notes

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