Triethylamine → 5-(2-(Trimethylsilyl)ethynyl)pyridin-2-amine

HRID 471397Notes

Reaction equation

HRID 471397 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:9][Si:10]([CH3:14])([CH3:13])[C:11]#[CH:12].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][Si:10]([C:11]#[C:12][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1)([CH3:14])[CH3:13]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 706222-Amino-5-bromopyridine

Product 1

HCID 224828585-(2-(Trimethylsilyl)ethynyl)pyridin-2-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 5.0 g (28.9 mmol) 5-bromo-pyridin-2-ylamine and 5.7 mL (40.5 mmol) 1-trimethylsilyl-ethyne using 168 mg (0.88 mmol) CuI, 758 mg (2.9 mmol) triphenylphosphine, 533 mg (0.76 mmol) PdCl2(PPh3)2 and 40 mL (288 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 hexane/ethyl acetate (10/1 v/v). Yield: 5.0 g (91%).

Workup

  1. extractionthe organic phase is extracted with water and brine
  2. customThe product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-833f0aa6cbbf4e019e759c3cd6c1c946
Source dataset
uspto-grants-2014_01
Patent number
US08633183B2

Reaction notes

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