Triethylamine → Methyl-(5-trimethylsilanylethynyl-pyridin-2-yl)-amine

HRID 1529197Notes

Reaction equation

HRID 1529197 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH3:9])=[N:6][CH:7]=1.[CH3:10][Si:11]([CH3:15])([CH3:14])[C:12]#[CH:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C.C1CCCCC1.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>[CH3:9][NH:8][C:5]1[CH:4]=[CH:3][C:2]([C:13]#[C:12][Si:11]([CH3:15])([CH3:14])[CH3:10])=[CH:7][N:6]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 156456635-Bromo-N-methylpyridin-2-amine

Product 1

HCID 66705950Methyl-(5-trimethylsilanylethynyl-pyridin-2-yl)-amine

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound is synthesized according to general procedure GP2 starting from 4.3 g (23.0 mmol) 5-bromo-2-methylamino-pyridine and 4.5 mL (32.2 mmol) 1-trimethylsilyl-ethyne using 134 mg (0.71 mmol) CuI, 601 mg (2.3 mmol) triphenylphosphine, 420 mg (0.60 mmol) PdCl2(PPh3)2 and 32 mL (101 mmol) triethylamine in 40 mL dry THF. For the work-up the reaction mixture is diluted with ethyl acetate and small amounts of cyclohexane, the organic phase is extracted with water and brine. The product is purified by chromatography on silica gel using a hexane/ethyl acetate gradient. Yield: 4.0 g (85%). Note: Sublimation of the product is observed at 40° C./40 mbar.

Workup

  1. extractionthe organic phase is extracted with water and brine
  2. customThe product is purified by chromatography on silica gel using a hexane/ethyl acetate gradient
  3. customis observed at 40° C.

Sources & evidence

ORD record
ord-2313b85f44514741b65847c75fcf46f6
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

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