Trimethylsilylacetylene → HCID 58235284, compound

HRID 1098588Notes

Reaction equation

HRID 1098588 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])#[CH:10]>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.[Cu]I>[CH3:12][Si:11]([CH3:14])([CH3:13])[C:9]#[C:10][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 58235284HCID 58235284, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

5-Bromopyridin-3-amine (0.94 g, 5.43 mmol), PdCl2(PPh3)2 (0.076 g, 0.109 mmol) and ethynyltrimethylsilane (0.64 g, 6.52 mmol) were combined in TEA (12.0 mL). After stirring for 5 min, CuI (0.010 g, 0.054 mmol) was added. The reaction mixture was flushed with N2 and stirred at RT overnight, followed by at 55° C. overnight. The reaction was filtered and the solid was washed with EtOAc (30 mL). The combined organics were concentrated in vacuo and purified by chromatography to afford 5-(2-(trimethylsilyl)ethynyl)pyridin-3-amine (0.279 g, 27% yield) as a white solid. MS (ESI) m/z: 191.1 (M+H+).

Workup

  1. customThe reaction mixture was flushed with N2
  2. stirringstirred at RT overnight
  3. customfollowed by at 55° C. overnight
  4. filtrationThe reaction was filtered
  5. washthe solid was washed with EtOAc (30 mL)
  6. concentrationThe combined organics were concentrated in vacuo
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-86c143eacbe64d0992ed34f1a9e9411d
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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