Propargyl alcohol → HCID 6482389, compound

HRID 2299301Notes

Reaction equation

HRID 2299301 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:21])[C:12]3[CH:19]=[C:18](I)[S:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[CH2:24]([OH:27])[C:25]#[CH:26]>[Cu](I)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>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:21])[C:12]3[CH:19]=[C:18]([C:26]#[C:25][CH2:24][OH:27])[S:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 10095695HCID 10095695, compound

Product 1

HCID 6482389HCID 6482389, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

To a suspension of N-(4-chlorobenzyl)-2-iodo-7-methyl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxamide (Example No. 23) (1.632 g) in diethylamnine (40 mL) is added copper iodide (0.210 g) and Pd(PPh3)2Cl2 (0.125 g) followed by addition of propargyl alcohol (0.29 mL). The reaction is stirred at rt for 18 h. The diethylamine is removed in vacuo and the resulting brown solid is purified via column chromatography (CH2Cl2:CH3OH; 98:2). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield an orange solid which is recrystallized from ethanol to yield 1.06 g (77%) of the title compound as a yellow solid.

Workup

  1. customThe diethylamine is removed in vacuo
  2. customthe resulting brown solid is purified via column chromatography (CH2Cl2:CH3OH; 98:2)
  3. concentrationconcentrated in vacuo
  4. customto yield an orange solid which
  5. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-f9abbc4569734a36a1ce21b018808f3a
Source dataset
uspto-grants-2002_12
Patent number
US06495683B2

Reaction notes

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