Sodium Carbonate → 4-(2-fluoropyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1042259

Reaktionsgleichung

Reaktionsgleichung von HRID 1042259
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:11][C:12]1[C:17](B(O)O)=[CH:16][CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[F:11][C:12]1[C:17]([C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:16][CH:15]=[CH:14][N:13]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Produkt 1

HCID 596273704-(2-fluoropyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidineAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (7.68 g, 50 mmol), 2-fluoropyridin-3-ylboronic acid (10.57 g, 75 mmol), and tetrakis(triphenylphosphine)palladium(0) (2.89 g, 2.5 mmol) was suspended in DME (300 mL) and aqueous sodium carbonate (10%) (50 mL, 100 mmol). The suspension was heated at reflux over night, cooled to r.t. and the reaction mixture was partitioned between EtOAc (300 mL) and NaHCO3 (aq., sat., 200 mL). The aqueous layer was washed with EtOAc twice. The organic layers were combined and washed with brine, then loaded on silica and purified via flash column (EtOAc:hexane=50-95%) on ISCO to give 4-(2-fluoropyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine as a light yellow solid with a green tint (1.85 g, 17% yield). MS (ESI, pos. ion) m/z: 214 [M+H]+

Aufarbeitung

  1. temperatureThe suspension was heated
  2. temperatureat reflux over night
  3. customthe reaction mixture was partitioned between EtOAc (300 mL) and NaHCO3 (aq., sat., 200 mL)
  4. washThe aqueous layer was washed with EtOAc twice
  5. washwashed with brine
  6. custompurified via flash column (EtOAc:hexane=50-95%) on ISCO

Quellen und Nachweise

ORD-Eintrag
ord-f56f02f51a004aaa8565503a101a2944
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557830B2

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