Dimethylamine → HCID 59453399, compound

HRID 714554Notes

Reaction equation

HRID 714554 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][N: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>[N:23]1[CH:24]=[CH:25][C:20]([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:21][CH:22]=1

Participants

9

Reactant 4

HCID 674DimethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 59453397HCID 59453397, compound

Product 1

HCID 59453399HCID 59453399, compoundYield 39%

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-pyridin-4-yl-1H-pyridazin-4-one (example 97, 81 mg, 0.21 mmol), ethynyltrimethylsilane (44 ul, 0.31 mmol), CuI (2 mg, 0.01 mmol), (PPh3)2PdCl2 (9 mg, 0.01 mmol), PPh3 (113 mg, 0.41 mmol) and dimethylamine (421 ul, 3.1 mmol of a solution in ethanol) in DMF (1.0 ml) is heated at 120° C. for 20 minutes under microwave irradiation. After purification of the crude product by preparative HPLC 33 mg (39% yield) of the product is obtained as solid material. MS: M=412.3 (M+H)+

Sources & evidence

ORD record
ord-10de37b4b6bc4e38a391b419f1e9c473
Source dataset
uspto-grants-2015_11
Patent number
US09187455B2

Reaction notes

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