Dimethylformamide → HCID 86680837, compound

HRID 2401695Notes

Reaction equation

HRID 2401695 reaction equation
I[C:2]1[C:3]([OH:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:13]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)#[CH:14].C(N(CC)CC)C.CN(C=O)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.O>[N:18]1[CH:19]=[CH:20][C:15]([C:13]2[O:12][C:3]3=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]3[CH:14]=2)=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 6428014-EthynylpyridineHCID 178517752HCID 178517752, compound

Product 1

HCID 86680837HCID 86680837, compoundYield 12.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 0.29 g of 3-iodo-5-(trifluoromethyl)pyridin-2-ol, 0.35 g of 4-ethynylpyridine, 20 mg of dichlorobis(triphenylphosphine)palladium(II), 0.30 g of triethylamine, 15 mg of copper(I) iodide and 5 ml of DMF was stirred under a nitrogen atmosphere at room temperature for 2 hours. To the reaction mixture were added water, then t-butyl methyl ether, and the mixture was filtered through Celite (registered trademark). The filtrate was separated, and the organic layer was dried over sodium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel preparative thin-layer chromatography to obtain 33 mg of 2-(pyridin-4-yl)-5-trifluoromethyl-furo[2,3-b]pyridine (hereinafter, referred to as “Present Active Compound 13”).

Workup

  1. filtrationt-butyl methyl ether, and the mixture was filtered through Celite (registered trademark)
  2. customThe filtrate was separated
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8c5f652b28714d81b57bf7126d931c0d
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

Loading…