Potassium Carbonate → HCID 66764966, compound

HRID 1466818Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([S:13][C:14]2[C:22]3[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=3)[NH:16][C:15]=2[CH3:24])[CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([S:13][C:14]2[C:22]3[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=3)[N:16]([C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)[C:15]=2[CH3:24])[CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: 170 °C

Procedure

3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-4-methoxy-benzoic acid ethyl ester (0.175 g, 0.466 mmol) was combined with CuO (3.71 mg, 0.046 mmol), potassium carbonate (0.0805 g, 0.582 mmol) and 3-bromopyridine (0.229 mL, 2.33 mmol) in DMF (250 μL) and the reaction was heated to 170° C. overnight. After cooling the reaction was submitted to standard aqueous workup and the residue was purified by silica gel chromatography (0-100% (EtOAc:MeOH 98:2) in hexanes) to give the title compound.

Workup

temperatureAfter cooling the reaction
customthe residue was purified by silica gel chromatography (0-100% (EtOAc:MeOH 98:2) in hexanes)

Sources & evidence

ORD record: ord-69c888b7391149f8b691039ded8a867c
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000025B2

Reaction notes

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