Potassium Carbonate → 4-oxo-N-(5-phenyl-1H-indol-6-yl)-1H-quinoline-3-carboxamide

HRID 74097Notes

Reaction equation

HRID 74097 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][C:12]([C:14]1[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=1)=[O:13])[NH:7][CH:6]=[CH:5]2.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:24]=[C:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=[C:14]1[C:12]([NH:11][C:10]1[CH:9]=[C:8]2[C:4]([CH:5]=[CH:6][NH:7]2)=[CH:3][C:2]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 57567304HCID 57567304, compound

Product 1

HCID 574702764-oxo-N-(5-phenyl-1H-indol-6-yl)-1H-quinoline-3-carboxamideYield 13%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of N-(5-bromo-1H-indol-6-yl)-4-oxo-1H-quinoline-3-carboxamide (B-27-I) (38 mg, 0.1 mol), phenyl boronic acid (18 mg, 0.15 mmol), (dppf)PdCl2 (cat.), and K2CO3 (100 μL, 2M solution) in DMF (1 mL) was heated in the microwave at 180° C. for 10 min. The reaction was filtered and purified by HPLC (10-99% CH3CN/H2O) to yield the product, 4-oxo-N-(5-phenyl-1H-indol-6-yl)-1H-quinoline-3-carboxamide (158) (5 mg, 13%). HPLC ret. time 3.05 min, 10-99% CH3CN, 5 min run; ESI-MS 380.2 m/z (MH+).

Workup

  1. filtrationThe reaction was filtered
  2. custompurified by HPLC (10-99% CH3CN/H2O)

Sources & evidence

ORD record
ord-902c69ee6b294d3eb5f36772b7c2fe08
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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