Propargyl alcohol → HCID 6482390, compound

HRID 1978952Notes

Reaction equation

HRID 1978952 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[CH:21]=[C:20](I)[S:19][C:13]=3[N:14]([CH:16]([CH3:18])[CH3:17])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[CH2:26]([OH:29])[C:27]#[CH:28]>C(NCC)C.[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:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[CH:21]=[C:20]([C:28]#[C:27][CH2:26][OH:29])[S:19][C:13]=3[N:14]([CH:16]([CH3:18])[CH3:17])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 7859Propargyl alcoholHCID 11755179HCID 11755179, compound

Product 1

HCID 6482390HCID 6482390, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

To a suspension of N-(4-chlorobenzyl)-2-iodo-7-isopropyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (Example No. 26) (0.717 g) in diethylamine (20 mL) is added copper iodide (0.084 g) and Pd(PPh3)2Cl2 (0.052 g) followed by addition of propargyl alcohol (0.12 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 then methanol to yield 0.281 g (46%) of the title compound as a yellow, crystalline 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-e2e2c2d9b5a34cd997d243f84bdaa5cc
Source dataset
uspto-grants-2001_05
Patent number
US06239142B1

Reaction notes

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