Ethyl Acetate → 3-(3-Bromo-phenylsulfanyl)-6-chloro-2-methyl-1-pyridin-2-yl-1H-indole

HRID 1466802Notes

Reaction equation

HRID 1466802 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH3:19])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].F[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1.CCOC(C)=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=3)[N:11]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[C:10]=2[CH3:19])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 97462-FluoropyridineHCID 11430Potassium CarbonateHCID 667653273-(3-Bromo-phenylsulfanyl)-6-chloro-2-methyl-1H-indole

Product 1

HCID 667649543-(3-Bromo-phenylsulfanyl)-6-chloro-2-methyl-1-pyridin-2-yl-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3-Bromo-phenylsulfanyl)-6-chloro-2-methyl-1H-indole (0.500 g, 1.4 mmol) along with K2CO3 (0.488 g, 3.5 mmol) and 2-fluoropyridine (87 μL, 2.1 mmol) were dissolved in DMF (2 mL) and reacted in a microwave at 200° C. for 20 minutes. The reaction was returned to the microwave at 200° C. for an additional 10 minutes. Standard workup followed by silica gel chromatography (0-100% EtOAc in hexanes) afforded the title compound.

Workup

  1. customreacted in a microwave at 200° C. for 20 minutes

Sources & evidence

ORD record
ord-bad232a3ad154979888dce215bb20d1f
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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