Water → 4-Methyl-3-(1-morpholinophthalazin-6-yl)benzoic acid

HRID 2357597Notes

Reaction equation

HRID 2357597 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[N:7][N:6]=[CH:5]2.[CH3:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)C.CCOC(C)=O>[CH3:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]=1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[N:7][N:6]=[CH:5]2

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 160860864-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acidHCID 251294786-Bromo-1-morpholinophthalazine

Product 1

HCID 251930634-Methyl-3-(1-morpholinophthalazin-6-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Bromo-1-morpholinophthalazine (191 mg, 649 μmol), 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (170 mg, 649 μmol), and tetrakis (triphenylphosphine)palladium (75 mg, 65 μmol) were added to a microwave vial before sodium carbonate-2 N in water (1.9 mL, 3892 μmol) and ethanol (3.2 mL) were added. The reaction mixture was reacted in a microwave oven for 10 min at 160° C. The reaction was cooled, diluted with 50 mL of EtOAc, added to an addition funnel and partitioned with sodium bicarbonate (saturated, aqueous). The organic layer was washed 2 times with 50 mL of sodium bicarbonate (saturated, aqueous), and separated. The aqueous layer was acidified to pH 5 with conc. HCl and extracted 4 times with 50 mL of chloroform. The organic layers were combined, dried over sodium sulfate, and concentrated via rotovap to give the title compound. Found MS (ES+): 350 (M+H)+.

Workup

  1. additionwere added
  2. customThe reaction mixture was reacted in a microwave oven for 10 min at 160° C
  3. temperatureThe reaction was cooled
  4. additionadded to an addition funnel
  5. custompartitioned with sodium bicarbonate (saturated, aqueous)
  6. washThe organic layer was washed 2 times with 50 mL of sodium bicarbonate (saturated, aqueous)
  7. customseparated
  8. extractionextracted 4 times with 50 mL of chloroform
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-9e7c5d452dc448c4978049b0001f30ee
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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