Potassium Carbonate → N-cyclopropyl-3-(1-(ethylthio)phthalazin-6-yl)-4-methylbenzamide

HRID 2357612Notes

Reaction equation

HRID 2357612 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([S:12][CH2:13][CH3:14])=[N:7][N:6]=[CH:5]2.[CH:15]1([NH:18][C:19](=[O:36])[C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[C:22](B3OC(C)(C)C(C)(C)O3)[CH:21]=2)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.CCO.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:15]1([NH:18][C:19](=[O:36])[C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[C:8]([S:12][CH2:13][CH3:14])=[N:7][N:6]=[CH:5]4)[CH:21]=2)[CH2:16][CH2:17]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 684548926-Bromo-1-(ethylthio)phthalazine

Product 1

HCID 68455798N-cyclopropyl-3-(1-(ethylthio)phthalazin-6-yl)-4-methylbenzamide

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 20074477Dimethoxyethane ethanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-bromo-1-(ethylthio)phthalazine (1.87 g), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.3 g, 0.9 mmol), and tetrakis(triphenylphosphine) palladium(0) (0.05 g, 0.05 mmol) in DME/EtOH (4:1) (5 mL) was treated with the 2 M aqueous solution of potassium carbonate (1 mL, 3 mmol). The mixture was heated at 90° C. for 1 h. The mixture was cooled, diluted with ethyl acetate (100 mL), washed with water (3×20 mL), brine 20 mL, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by chromatography eluting with 1-5% 2 M ammonia methanol/dichloromethane to give the title compound as pale yellow solid. Found MS(ES+): 364(M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water (3×20 mL), brine 20 mL
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by chromatography
  6. washeluting with 1-5% 2 M ammonia methanol/dichloromethane

Sources & evidence

ORD record
ord-3a9e10be422e48c5a4eebc0a18a718f6
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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