Triethylamine → HCID 58235284, compound

HRID 1907164Notes

Reaction equation

HRID 1907164 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:35][Si:36]([C:39]#[CH:40])([CH3:38])[CH3:37]>C1COCC1.[Cu]I.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.C(Cl)Cl>[CH3:35][Si:36]([C:39]#[C:40][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1)([CH3:38])[CH3:37]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 58235284HCID 58235284, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 7.23 g (41.8 mmol) 5-bromo-3-amino-pyridine in 70 mL dry THF under argon atmosphere is added 239 mg (1.3 mmol) CuI, 880 mg (1.3 mmol) bis(triphenyl-phosphine)palladium(II) chloride, 1.1 g (4.2 mmol) triphenylphosphine and 70 mL (0.50 mol) triethylamin. Then 8.3 mL (59 mmol) trimethylsilylacetylene are added and the reaction mixture is heated at 75° C. over night. After cooling to RT, 100 mL DCM is added and the reaction mixture is extracted twice with 100 mL water. The organic layer is dried over MgSO4 and the product is purified by chromatography on silica gel. Yield: 5.26 g (66%).

Workup

  1. temperatureAfter cooling to RT
  2. extractionthe reaction mixture is extracted twice with 100 mL water
  3. dry with materialThe organic layer is dried over MgSO4
  4. customthe product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-80073d37e5c04eab87f4d991a55a5b1f
Source dataset
uspto-grants-2013_12
Patent number
US08598157B2

Reaction notes

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