Triphenylphosphine → 2-(5-Chloropyridin-2-yl)furo[3,2-c]pyridin-4(5H)-one

HRID 60385Notes

Reaction equation

HRID 60385 reaction equation
Br[C:2]1[O:10][C:9]2[CH:8]=[CH:7][NH:6][C:5](=[O:11])[C:4]=2[CH:3]=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([B-]23OCC(C)(CO2)CO3)=[N:17][CH:18]=1.[Li+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I.CC(N(C)C)=O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:2]2[O:10][C:9]3[CH:8]=[CH:7][NH:6][C:5](=[O:11])[C:4]=3[CH:3]=2)=[N:17][CH:18]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 747877752-bromofuro[3,2-c]pyridin-4(5H)-oneHCID 131737090Lithium 1-(5-chloropyridin-2-yl)-4-methyl-2,6,7-trioxa-1-borabicyclo[2.2.2]octan-1-uide

Product 1

HCID 1179496192-(5-Chloropyridin-2-yl)furo[3,2-c]pyridin-4(5H)-oneYield 29.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
250 °C

Procedure

A mixture of 2-bromofuro[3,2-c]pyridin-4(5H)-one (200 mg), lithium 1-(5-chloropyridin-2-yl)-4-methyl-2,6,7-trioxa-1-borabicyclo[2.2.2]octan-1-uide (462 mg), palladium(II) acetate (21.0 mg), copper(I) iodide (178 mg), triphenylphosphine (49.0 mg) and DMA (1.0 mL) was heated at 250° C. for 30 min under microwave irradiation. The reaction mixture was purified by silica gel column chromatography (NH, methanol/ethyl acetate), and the obtained solid was washed with diisopropyl ether to give the title compound (69.0 mg) as a white solid.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (NH, methanol/ethyl acetate)
  2. washthe obtained solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-a5b547294aa6426899d98b6f131425ae
Source dataset
uspto-grants-2016_09
Patent number
US09440987B2

Reaction notes

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