Dimethylamine → HCID 59369982, compound

HRID 1924509Notes

Reaction equation

HRID 1924509 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[C:18](=[O:19])[CH:17]=[CH:16][N:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:14]=3)=[CH:11][CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:26]([Si:28]([CH3:31])([CH3:30])[CH3:29])#[CH:27].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CNC>C(O)C.CN(C=O)C.[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>[C:20]1([N:15]2[CH:16]=[CH:17][C:18](=[O:19])[C:13]([C:12]3[N:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([C:27]#[C:26][Si:28]([CH3:31])([CH3:30])[CH3:29])[CH:3]=4)[N:9]=[CH:10][CH:11]=3)=[N:14]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 4

HCID 674DimethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 46219320HCID 46219320, compound

Product 1

HCID 59369982HCID 59369982, compoundYield 55.4%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-[2-(3-bromo-phenyl)-2H-pyrazol-3-yl]-1-phenyl-1H-pyridazin-4-one (example 23, 87 mg, 0.22 mmol), ethynyltrimethylsilane (47 ul, 0.33 mmol), CuI (3 mg, 0.01 mmol), (PPh3)2PdCl2 (10 mg, 0.01 mmol), PPh3 (122 mg, 0.44 mmol) and dimethylamine (596 ul, 3.3 mmol of a solution in ethanol) in DMF (0.9 ml) is heated at 120° C. for 20 minutes under microwave irradiation. After purification of the crude product by preparative HPLC 50 mg (55% yield) of the product is obtained as solid material.

Sources & evidence

ORD record
ord-5d4fdec370e640e684d3108e01b6175d
Source dataset
uspto-grants-2012_05
Patent number
US08178538B2

Reaction notes

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