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

HRID 471398Notes

Reaction equation

HRID 471398 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%).

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

Sources & evidence

ORD record
ord-71264766d05b432a907f6194ca01b16a
Source dataset
uspto-grants-2014_01
Patent number
US08633183B2

Reaction notes

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