Diisopropylamine → 4-(7-Bromo-3-isoquinolinyl)benzonitrile

HRID 2390406Notes

Reaction equation

HRID 2390406 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6](/[CH:8]=[N:9]/[C:10]([CH3:13])([CH3:12])C)[CH:7]=1.[C:15]([C:17]1[CH:22]=[CH:21]C(C#C)=[CH:19][CH:18]=1)#[N:16].C(NC(C)C)(C)C>C1(C)C=CC=CC=1.[Cu]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>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([CH:13]=[C:10]([C:12]3[CH:21]=[CH:22][C:17]([C:15]#[N:16])=[CH:18][CH:19]=3)[N:9]=[CH:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 45472454-EthynylbenzonitrileHCID 178448919HCID 178448919, compound

Product 1

HCID 671042584-(7-Bromo-3-isoquinolinyl)benzonitrile

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

The product from Example 62D (3.6 mmol), 4-cyanophenylacetylene (4.3 mmol), CuI (0.2 mmol), PdCl2(PPh3)2 (0.1 mmol), and diisopropylamine (5.3 mmol) can be combined in toluene (15 mL) and processed as described in Example 62E to provide the title compound.

Sources & evidence

ORD record
ord-1178ac53b86445799ddf47cda10da5c3
Source dataset
uspto-grants-2012_09
Patent number
US08273767B2

Reaction notes

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