Triethylamine → HCID 58235284, compound

HRID 1258421Notes

Reaction equation

HRID 1258421 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 stirred solution of 7.23 g (41.8 mmol) 5-bromo-3-amino-pyridine in 70 mL dry THF under argon atmosphere is added 238.8 mg (1.3 mmol) CuI, 880 mg (1.3 mmol) bis(triphenylphosphine)palladium(II) chloride, 1.1 g (4.2 mmol) triphenylphosphine and 70 mL (501 mmol) triethylamin. Then 8.3 mL (58.5 mmol) trimethylsilylethyne are added and the reaction 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 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 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-2261a2c79ed7463393281b8728354b55
Source dataset
uspto-grants-2013_06
Patent number
US08466162B2

Reaction notes

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