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

HRID 551552Notes

Reaction equation

HRID 551552 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-b4543ed2f70449f58d2f4ed17720778e
Source dataset
uspto-grants-2011_05
Patent number
US07947711B2

Reaction notes

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