Chloroacetyl chloride → 6-Bromo-4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-1-[(4-methylphenyl)sulfonyl]-1H-indazole

HRID 520504Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([C:21]2[NH:25][N:24]=NN=2)[CH:3]=1.[Cl:26][CH2:27][C:28](Cl)=[O:29]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)(=[O:12])=[O:13])=[C:4]([C:21]2[O:29][C:28]([CH2:27][Cl:26])=[N:24][N:25]=2)[CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A stirred mixture of 6-bromo-1-[(4-methylphenyl)sulfonyl]-4-(1H-tetrazol-5-yl)-1H-indazole (0.237 g, 0.565 mmol) and chloroacetyl chloride (0.136 ml, 1.696 mmol) in toluene (3 ml) was heated at 130° C. in the microwave (biotage initiator) for 20 mins. The solvent was removed in vacuo and triturated with ether (10 ml) to give the title compound as a colourless solid (0.18 g).

Workup

customThe solvent was removed in vacuo
customtriturated with ether (10 ml)

Sources & evidence

ORD record: ord-4260642f1cf84d8e9348fd26484de9a8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326987B2

Reaction notes

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