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

HRID 860882Notes

Reaction equation

HRID 860882 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-305378bf99bd4b7f9e759f059ae4b967
Source dataset
uspto-grants-2006_12
Patent number
US07153889B2

Reaction notes

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