Sodium Carbonate → 6-(3-Hydroxyphenyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 64376

Reaktionsgleichung

Reaktionsgleichung von HRID 64376
Br[C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)[C:10]=2[C:11]#[N:12])[CH:7]=1.[OH:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[OH:26][C:27]1[CH:32]=[C:31]([C:2]2[CH:3]=[N:4][C:5]3[N:6]([N:8]=[C:9]([C:13]4[CH:18]=[CH:17][C:16]([O:19][C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:15][CH:14]=4)[C:10]=3[C:11]#[N:12])[CH:7]=2)[CH:30]=[CH:29][CH:28]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 1176680926-Bromo-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Produkt 1

HCID 1176681096-(3-Hydroxyphenyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrileAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 6-bromo-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (782 mg, 2.0 mmol) in dioxane (10 mL) and H2O (10 mL) was added 3-hydroxyphenylboronic acid (276 mg, 2.0 mmol), Pd(PPh3)4 (240 mg, 0.2 mmol) and Na2CO3 (424 mg, 4.0 mmol). After stirring at 65° C. under N2 for 16 hr, the mixture was concentrated and 100 mL of DCM, 10 mL of CH3OH, 100 mL of H2O were added. Organic layers were separated from aqueous layers and dried over Na2SO4 and purified by chromatography column on silica gel eluting with DCM/CH3OH to afford 500 mg (62%) of 6-(3-hydroxyphenyl)-2-(4-phenoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile as a yellow solid. MS (ESI) m/e [M+1]+ 404.9.

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. addition100 mL of DCM, 10 mL of CH3OH, 100 mL of H2O were added
  3. customOrganic layers were separated from aqueous layers
  4. dry with materialdried over Na2SO4
  5. custompurified by chromatography column on silica gel eluting with DCM/CH3OH

Quellen und Nachweise

ORD-Eintrag
ord-ef099b0ab4d746cc97e8ec35a5a8e201
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447106B2

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