Triethylamine → 5-Fluoro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

HRID 490463Notes

Reaction equation

HRID 490463 reaction equation
[F:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])#[CH:11].[Cl-].[Li+].C(N(CC)CC)C>CN(C)C=O.[Cu](I)I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:11]#[C:10][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:5]([NH2:8])=[N:6][CH:7]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 433294Lithium ChlorideHCID 184559742-Amino-5-fluoro-3-iodopyridine

Product 1

HCID 597068495-Fluoro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

But using 14 g of 5-fluoro-3-iodopyridin-2-ylamine, 12.47 ml of ethynyltrimethylsilane, 2.24 g of copper iodide, 2.74 g of lithium chloride, 41.33 ml of triethylamine and 2.15 g of [1,1′-bis(diphenylphosphino)ferrocene] palladium(II) chloride in 441 ml of dimethylformamide. After flash chromatography on a silica column (eluent: dichloromethane), 7.91 g of 5-fluoro-3-trimethylsilanylethynylpyridin-2-ylamine are thus obtained in the form of a solid, the characteristics of which are as follows:

Sources & evidence

ORD record
ord-40d8c0aa1d10499e8ea56d4e7056b3cd
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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