Triethylamine → 4-(phenylethynyl)phthalazin-1(2H)-one

HRID 469654Notes

Reaction equation

HRID 469654 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][N:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)#[CH:14].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O.[Cu]I.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>[C:15]1([C:13]#[C:14][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:12])[NH:4][N:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 27751424-chlorophthalazin-1(2H)-one

Product 1

HCID 671600474-(phenylethynyl)phthalazin-1(2H)-one

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chlorophthalazin-1(2H)-one, ethynylbenzene, triethylamine, copper(I) iodide, and Pd(PPh3)4 in DMF was microwaved at 185° C. for 30 minutes, diluted with EtOAc, washed with water and saturated aqueous NH4Cl, and chromatographed to give impure 4-(phenylethynyl)phthalazin-1(2H)-one, which was used without further purification. This material was treated with O-(diphenylphosphoryl)hydroxylamine as in Example 1B to give impure 2-amino-4-(phenylethynyl)phthalazin-1(2H)-one.

Workup

  1. customwas microwaved at 185° C. for 30 minutes
  2. washwashed with water and saturated aqueous NH4Cl
  3. customchromatographed

Sources & evidence

ORD record
ord-b86240d534ed42f280b6a3a9eef7059a
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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