Methanesulfonamide → 5-bromo-6-chloro-N-(methylsulfonyl)-1H-indole-3-carboxamide

HRID 338545Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[CH:12]=[O:13].C(C(OC1C(OC(C(C)(C)C)=O)=C(I)C=CC=1)=O)(C)(C)C.[CH3:35][S:36]([NH2:39])(=[O:38])=[O:37]>C(OC(C)C)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[C:12]([NH:39][S:36]([CH3:35])(=[O:38])=[O:37])=[O:13]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 5-bromo-6-chloro-1H-indole-3-carbaldehyde (445 mg, 1.72 mmol), Bis(tert-butylcarbonyloxy)iodobenzene (961 mg, 2.30 mmol) in isopropyl acetate (2 mL) was added methanesulfonamide (111 mg, 1.15 mmol). After stirring 5 minutes, Bis[rhodium(α,α,α′,α′-tetramethyl-1,3-benzenedipropionic acid)] (18.3 mg, 0.0230 mmol) was added and heated to 50° C. for 2 h. The reaction was filtered and the collected solid (245 mg) was identified as a mixture of the title compound and 5-bromo-6-chloro-1H-indole-3-carbaldehyde. The mixture was taken forward without any further purification.

Workup

filtrationThe reaction was filtered
additionthe collected solid (245 mg) was identified as a mixture of the title compound and 5-bromo-6-chloro-1H-indole-3-carbaldehyde
customThe mixture was taken forward without any further purification

Sources & evidence

ORD record: ord-b5fb19cb1edf41549481f1e77a28f25e
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889730B2

Reaction notes

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