1,4-Dioxane → 5-(4-Pyridinyl)-1H-indole-2-carboxylic acid

HRID 2098452Notes

Reaction equation

HRID 2098452 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[N:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.O1CCOCC1>Cl[Pd]Cl.O>[N:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]3)=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 2521375-Bromo-1H-indole-2-carboxylic acidHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 582865285-(4-Pyridinyl)-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Procedure

A solution of 5-bromo-1H-indole-2-carboxylic acid (25 mg), PdCl2 HPNor2 (5 mg), K3PO4 (45 mg), 4-pyridylboronic acid (26 mg), dioxane (1 mL) and H2O (1 mL) was heated to 170° C. in a microwave for 2 h. The solution was passed thru a C18-SPE cartridge eluting with 3, 20, 60, and finally 95% CH3CN in H2O to yield the crude product. LCMS (m/z): 239.1 (M+H).

Workup

  1. washeluting with 3, 20, 60, and finally 95% CH3CN in H2O

Sources & evidence

ORD record
ord-5a183b0913714c8a8faaca6ba8c46aae
Source dataset
uspto-grants-2013_05
Patent number
US08450484B2

Reaction notes

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