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

HRID 38840Notes

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.[C:26](Cl)(=[O:28])[CH3:27]>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:28][C:26]([CH3:27])=[N:24][N:25]=2)[CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A stirred mixture of 6-Bromo-1-[(4-methylphenyl)sulphonyl]-4-(1H-tetrazol-5-yl)-1H-indazole (300 mg, 0.615 mmol) and acetyl chloride (0.722 ml, 10.15 mmol) in toluene (10 ml) were heated under microwave irradiation at 130° C. for 20 mins. The reaction mixture was heated for a further 20 mins at 130° C. then evaporated to dryness. The resultant yellow solid was treated with methanol (10 ml), to give a beige solid and supernatant. The supernatant was pipetted off, the process repeated twice and the resultant solid dried under vacuum to give the title compound as a beige solid (75 mg).

Workup

temperatureThe reaction mixture was heated for a further 20 mins at 130° C.
customthen evaporated to dryness
additionThe resultant yellow solid was treated with methanol (10 ml)
customto give a beige solid
customthe resultant solid dried under vacuum

Sources & evidence

ORD record: ord-438cd2a4c9fa45a9930fb00a74f49a37
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524751B2

Reaction notes

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