Sodium Carbonate → 4-(3,6-dihydro-2H-pyran-4-yl)phthalazin-1(2H)-one

HRID 535484Notes

Reaction equation

HRID 535484 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.[O:13]1[CH2:18][CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH2:15][CH2:14]1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O.CCOC(C)=O.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>[O:13]1[CH2:14][CH:15]=[C:16]([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)[CH2:17][CH2:18]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27751424-chlorophthalazin-1(2H)-oneHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

Product 1

HCID 709762134-(3,6-dihydro-2H-pyran-4-yl)phthalazin-1(2H)-one

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 4-chlorophthalazin-1(2H)-one (150 mg, 0.831 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (174 mg, 0.831 mmol), Na2CO3 (164 mg, 2.49 mmol) and Pd(PPh3)4 (47.8 mg, 0.042 mmol) in DMF (3 mL) and H2O (1 mL) was heated at 180° C. under microwave condition for 20 minutes. The mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3, dried (Na2SO4), filtered, and concentrated to afford the title compound: MS (APCI) M/Z 229 (M+H)+.

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-266f0e53f35d44598d87afd0e3c18f7b
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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