Propargyl alcohol → HCID 11255499, compound

HRID 917717Notes

Reaction equation

HRID 917717 reaction equation
[F:1][C:2]1[CH:19]=[C:18](I)[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[C:6]([C:13]([NH2:15])=[O:14])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1.[CH2:21]([OH:24])[C:22]#[CH:23]>CN(C=O)C.[Cu]I.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>[F:1][C:2]1[CH:19]=[C:18]([C:23]#[C:22][CH2:21][OH:24])[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[C:6]([C:13]([NH2:15])=[O:14])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1

Participants

6

Reactant 2

HCID 7859Propargyl alcoholHCID 11338183HCID 11338183, compound

Product 1

HCID 11255499HCID 11255499, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

4-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide was reacted with propargyl alcohol in the presence of CuI, (Ph3P)2PdCl2 and TEA in DMF as for example 2. The residue resulting from removal of the reaction solvents under reduced pressure was purified by column chromatography on silica gel (5% MeOH/CH2Cl2 as eluant) to give 4-[2-fluoro-4-(3-hydroxy-1-propynyl)anilino]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide as an off-white solid (89%). 1H NMR [(CD3)2SO, 400 MHz] δ 10.57 (s, 1 H), 8.35 (s, 1H), 7.90 (br s, 1H), 7.50 (t, J=8.5 Hz, 1H), 7.48 (br s, 1H), 7.39 (dd, J=11.4, 1.8 Hz, 1H), 7.28 (dd, J=8.3, 1.5 Hz, 1H), 5.69 (s, 1H), 5.36 (t, J=6.0 Hz, 1H), 4.30 (d, J=5.9 Hz, 2H), 3.37 (s, 3H). LCMS (APCI+) calcd for C16H15FN3O3 316 (MH+), found 316.

Workup

  1. customThe residue resulting from removal of the reaction solvents under reduced pressure
  2. customwas purified by column chromatography on silica gel (5% MeOH/CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-aa5f858d30a048698d69fcf13c7dce87
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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