Potassium Carbonate → 3-(1-(2-chlorophenyl)phthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide

HRID 2357585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2357585
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:15]([NH:17][CH:18]3[CH2:20][CH2:19]3)=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>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.COCCOC.CCO>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:15]([NH:17][CH:18]3[CH2:19][CH2:20]3)=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 118483123-(1-chlorophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide

Produkt 1

HCID 118483723-(1-(2-chlorophenyl)phthalazin-6-yl)-N-cyclopropyl-4-methylbenzamideAusbeute 21,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 20074477Dimethoxyethane ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 3-(1-chlorophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide (0.11 g, 0.327 mmol), 2-chlorophenylboronic acid (51 mg, 329 μmol), 5 mL DME/EtOH (4:1), 0.5 mL 2M K2CO3 and tetrakis(triphenylphosphine)palladium (20mg) was stirred at 90° C. for 1 h. The reaction mixture was cooled to RT. The crude product was purified via flash chromatography (silica gel) with 2% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia in MeOH/DCM to give the crude compound (120 mg) as a yellow solid. The compound was further purified by HPLC by dissolving the crude product in methanol (˜20 mg/mL) and injecting at a rate of about 0.500 mL per injection onto the Gilson preparatory HPLC. Pure product fractions were collected, combined, basefied with sodium bicarbonate (saturated, aqueous), extracted with CH2Cl2, separated, dried over sodium sulfate, and concentrated via rotary evaporation to give pure title compound (28.8 mg) as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to RT
  2. customThe crude product was purified via flash chromatography (silica gel) with 2% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia in MeOH/DCM
  3. customto give the crude compound (120 mg) as a yellow solid
  4. customThe compound was further purified by HPLC
  5. dissolutionby dissolving the crude product in methanol (˜20 mg/mL)
  6. customPure product fractions were collected
  7. extractionextracted with CH2Cl2
  8. customseparated
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated via rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-640f421a670d477684b97200e0f9bd63
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759337B2

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