Dimethylformamide → HCID 44594044, compound

HRID 1776153Notes

Reaction equation

HRID 1776153 reaction equation
I[C:2]1[S:3][C:4]2[NH:5][C:6](=[O:15])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1.CN(C=O)C.[CH3:21][N:22]([CH3:26])[CH2:23][C:24]#[CH:25]>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.C(N(CC)CC)C>[CH3:21][N:22]([CH3:26])[CH2:23][C:24]#[C:25][C:2]1[S:3][C:4]2[NH:5][C:6](=[O:15])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 81643N,N-DimethylpropargylamineHCID 58016054HCID 58016054, compound

Product 1

HCID 44594044HCID 44594044, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

2-Iodo-1,3-thiazolo[5,4-c]isoquinolin-5(4H)-one (0.1 g, 0.3 mmol), DMF (10 ml), 1-dimethylamino-2-propyne (0.25 g, 3.05 mmol), (Ph3P)2PdCl2 (10 mg), CuI (1 mg), and triethylamine (1.2 ml) were stirred at room temperature for 4 hours. The solvent was removed under reduced pressure and the mixture was chromatographed on SiO2 gel, eluting, with dichloromethane/methanol (98/2), to produce the title compound. Yield: 68% yield.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe mixture was chromatographed on SiO2 gel
  3. washeluting, with dichloromethane/methanol (98/2)

Sources & evidence

ORD record
ord-841bdcc2dd1c43608ef064f82c443f96
Source dataset
uspto-grants-2016_02
Patent number
US09265769B2

Reaction notes

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