Propargyl alcohol → N-(4-chlorobenzyl)-2-(3-hydroxyprop-1-ynyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 982706Notes

Reaction equation

HRID 982706 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[S:19][C:18](I)=[CH: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]>CN(C=O)C.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl>[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[S:19][C:18]([C:26]#[C:25][CH2:24][OH:27])=[CH: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 22563223N-(4-chlorobenzyl)-2-iodo-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 10000250N-(4-chlorobenzyl)-2-(3-hydroxyprop-1-ynyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideYield 68.7%

Reagents, catalysts & solvents 2

HCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(4-chlorobenzyl)-2-iodo-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (0.20 g, 0.44 mmol), Pd(PhCN)2Cl2 (10 mg) CuI (7 mg) Et3N (1 mL) and propargyl alcohol (0.036 g, 0.66 mmol) in DMF was stirred at ambient temperature overnight. The solvent was removed and the residue partitioned between H2O and CH2Cl2 (100 mL each). The layers were shaken, the organic layer separated and dried over MgSO4. The solvents were removed in vacuo and the residue purified via flash column chromatography (eluant 5% MeOH/CH2Cl2) to afford 0.117 g title compound as a white solid.

Workup

  1. customThe solvent was removed
  2. customthe residue partitioned between H2O and CH2Cl2 (100 mL each)
  3. stirringThe layers were shaken
  4. customthe organic layer separated
  5. dry with materialdried over MgSO4
  6. customThe solvents were removed in vacuo
  7. customthe residue purified via flash column chromatography (eluant 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9a4e32aec016475bafe0df76622b7dea
Source dataset
uspto-grants-2005_03
Patent number
US06861438B2

Reaction notes

Loading…