Diisopropylethylamine → Benzoylhydrazine

HRID 570983Notes

Reaction equation

HRID 570983 reaction equation
C(C1N2C=CN=CC2=NC=1)#C.I[C:13]1[CH:14]=[C:15]([CH:31]=[CH:32][C:33]=1C)[C:16]([NH:18][NH:19]C(=O)C1C(Cl)=CC(Cl)=CC=1Cl)=[O:17].C(N(C(C)C)CC)(C)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:16]([NH:18][NH2:19])(=[O:17])[C:15]1[CH:31]=[CH:32][CH:33]=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 70560276N'-(3-iodo-4-methylbenzoyl)-2,4,6-trichlorobenzohydrazideHCID 722072723-Ethynyl-imidazo[1,2-A]pyrazine

Product 1

HCID 11955Benzoylhydrazine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-ethynylimidazo[1,2-a]pyrazine (0.09 g, 0.6 mmol), N′-(3-iodo-4-methylbenzoyl)-2,4,6-trichlorobenzohydrazide (0.3 g, 0.6 mmol), Pd(PPh3)4 (0.036 g, 0.03 mmol), CuI (0.008 g, 0.03 mmol) and diisopropylethylamine (0.75 ml, 0.9 mmol) in DMF (10 ml) was stirred at ambient temperature for 12 hrs under an atmosphere of nitrogen. The reaction mixture was concentrated and the crude product was purified by flash chromatography on silica gel (elution with 10% methanol in dichloromethane) to provide 2,4,6-trichloro-N′-[3-[2-(2-imidazo[1,2-a]pyrazin-3-yl)ethynyl)]]-4-methylbenzoyl]benzohydrazide.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude product was purified by flash chromatography on silica gel (elution with 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5efee2485d4647ff8ee415766240d1c7
Source dataset
uspto-grants-2015_05
Patent number
US09024021B2

Reaction notes

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