Triethylamine → HCID 71737536, compound

HRID 717111Notes

Reaction equation

HRID 717111 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[CH:15][CH:14]=1)[NH:6][C:7]2=[O:12].C(N(CC)CC)C.[CH2:32]([OH:36])[CH2:33][C:34]#[CH:35]>CN(C=O)C.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>[CH3:23][N:22]([CH3:24])[CH2:21][CH2:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:5]2[NH:6][C:7](=[O:12])[C:8]3[C:3]([CH:4]=2)=[C:2]([C:35]#[C:34][CH2:33][CH2:32][OH:36])[CH:11]=[CH:10][CH:9]=3)=[CH:14][CH:15]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 135663-Butyn-1-OLHCID 71735149HCID 71735149, compound

Product 1

HCID 71737536HCID 71737536, compoundYield 39%

Reagents, catalysts & solvents 3

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

Procedure

5-Bromo-3-[4-(2-dimethylaminoethoxy)phenyl]-2H-isoquinolin-1-one (50.0 mg, 0.130 mmol), triethylamine (1.1 mL, 8.36 mmol), dichlorobis(triphenylphosphine)palladium(II) (5.0 mg, 0.0065 mmol), copper (I) iodide (3.0 mg, 0.009 mmol), 3-butyn-1-ol (20 μL, 0.260 mmol) in DMF (1.1 mL) were added to a microwave vial and the reaction mixture purged with N2 for 5 min. The reaction mixture was irradiated using a microwave reactor (300 W, 100° C., 90 min). The reaction mixture was filtered through Celite® 545, diluted with DMSO and was purified by reverse phase preparative HPLC-MS to obtain 3-[4-(2-dimethylaminoethoxy)phenyl]-5-(4-hydroxybut-1-ynyl)-2H-isoquinolin-1-one as a brown solid (19.0 mg, 39%).

Workup

  1. customthe reaction mixture purged with N2 for 5 min
  2. customThe reaction mixture was irradiated
  3. custom(300 W, 100° C., 90 min)
  4. filtrationThe reaction mixture was filtered through Celite® 545
  5. additiondiluted with DMSO
  6. customwas purified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-aea3a420014e4e3397dd2b6f1587b5dd
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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