4-Bromobiphenyl → HCID 66764826, compound

HRID 1466798Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:32][CH:31]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[N:13]([C:39]3[CH:40]=[CH:41][C:36]([C:33]4[CH:34]=[CH:35][CH:30]=[CH:31][CH:32]=4)=[CH:37][CH:38]=3)[C:12]=2[CH3:21])[CH:5]=1

Participants

Conditions

Temperature: 170 °C

Procedure

3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (0.100 g, 0.3 mmol) was combined with CuO (0.0024 g, 0.03 mmol), potassium carbonate (0.041 g, 0.3 mmol) and 4-bromobiphenyl (0.0699 g, 0.3 mmol) in DMF (150 μL) and the reaction was heated to 170° C. overnight. After cooling the reaction was submitted to standard aqueous workup to give the title compound as a crude mixture that was taken directly to the next step without purification.

Workup

temperatureAfter cooling the reaction

Sources & evidence

ORD record: ord-acf6bd6f432940a9bf049a7955f34faf
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000025B2

Reaction notes

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