2-Bromopyridine → HCID 71563077, compound

HRID 1844390Notes

Reaction equation

HRID 1844390 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]#[C:13][C:14]([CH3:17])(O)C)=[N:7]2.[OH-].[K+].Br[C:21]1[CH:26]=[CH:25]C=C[N:22]=1.CCOC(C)=O.CCCCCC>C(NC(C)C)(C)C.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.[Cu]I>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]#[C:13][C:14]1[CH:17]=[CH:25][CH:26]=[CH:21][N:22]=1)=[N:7]2

Participants

8

Reactant 4

HCID 79732-BromopyridineHCID 14797Potassium HydroxideHCID 21226206Ethyl acetate hexaneHCID 71561383HCID 71561383, compound

Product 1

HCID 71563077HCID 71563077, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 7912DiisopropylamineSolvent

Conditions

Temperature
110 °C

Procedure

4-(5-Chloroquinoline-2-yl)-2-methylbut-3-yn-2-ol (24.5 mg, 0.0997 mmol), PdCl2(PPh3)2 (3.4 mg, 0.00484 mmol), CuI (1.2 mg, 0.00875 mmol), and KOH (44.6 mg, 0.795 mmol) were dissolved in diisopropylamine (0.2 mL) in a vial. The resulting mixture was stirred for 5 min under nitrogen atmosphere, followed by adding 2-bromopyridine (9.6 uL, 0.0997 mmol) thereto. After the vial was capped, it was heated to 110° C. The completion of the reaction was confirmed by TLC (EtOAc/Hexane=1:1). When the reaction was completed, the reactant was cooled down to room temperature and filtered through Celite and ethyl acetate. The thus obtained filtrate was extracted with ethyl acetate, to thereby obtain an organic layer. The organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (EtOAc/Hexane=1:1, R.f: 0.3), to thereby obtain 5-chloro-2-(pyridine-2-ylethynyl)quinoline (6.2 mg, 25%) as a brown solid.

Workup

  1. customAfter the vial was capped
  2. temperaturethe reactant was cooled down to room temperature
  3. filtrationfiltered through Celite and ethyl acetate
  4. extractionThe thus obtained filtrate was extracted with ethyl acetate
  5. customto thereby obtain an organic layer
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. custompurified by column chromatography (EtOAc/Hexane=1:1, R.f: 0.3)

Sources & evidence

ORD record
ord-ee829cdfd6c64af486d1b07c4ff442b8
Source dataset
uspto-grants-2015_02
Patent number
US08946431B2

Reaction notes

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