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Sodium Carbonate → 6-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-4'-fluorobiphenyl-3-carbonitrile

HRID 1877932
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1877932
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]1[N:14]2[CH:15]=[N:16][CH:17]=[C:13]2[CH2:12][CH2:11]1)[C:5]#[N:6].[F:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+].[OH-].[K+]>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>[CH:17]1[N:16]=[CH:15][N:14]2[CH:10]([C:9]3[C:2]([C:22]4[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=4)=[CH:3][C:4]([C:5]#[N:6])=[CH:7][CH:8]=3)[CH2:11][CH2:12][C:13]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 14797Potassium HydroxideHCID 2856454-Fluorophenylboronic acidHCID 588270573-bromo-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile

Produkt 1

HCID 588271906-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-4'-fluorobiphenyl-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a solution of 3-bromo-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile (0.100 g, 0.347 mmol) and 4-fluorophenylboronic acid (0.158 g, 1.04 mmol) in DME (2 mL), aqueous solutions of Na2CO3 (0.69 mL, 2 M) and KOH (0.17 mL, 2 M) are added. After degassing with nitrogen, Pd(PPh3)4 (0.040 g, 0.035 mmol) is added. Mixture is heated in a microwave reactor at 130° C., for 20 minutes. LCMS showed consumption of starting material. The solution is then diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The resulting aqueous layer is extracted further with ethyl acetate (3×). The combined organic layers are washed with brine and dried over anhydrous sodium sulfate. After concentration, crude product is purified by flash chromatography (Hexane/EtOAc, and then 10% MeOH/DCM) followed by preparative HPLC (0-50% acetonitrile with 0.1% TFA in 21 minutes). After concentration and free basing, 6-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-4′-fluorobiphenyl-3-carbonitrile is obtained as a white powder. MS (ESI) m/z 304.0 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm 2.38-2.54 (m, 1 H), 2.76-3.03 (m, 3 H), 5.33 (app t, J=6.7 Hz, 1 H), 6.79 (s, 1 H), 7.01 (d, J=8.1 Hz, 1 H), 7.15-7.24 (m, 3 H), 7.29 (dd, J=13.4, 5.1 Hz, 2 H), 7.54-7.65 (m, 2 H).

Aufarbeitung

  1. additionis added
  2. customconsumption of starting material
  3. additionThe solution is then diluted with ethyl acetate and saturated aqueous sodium bicarbonate
  4. extractionThe resulting aqueous layer is extracted further with ethyl acetate (3×)
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationAfter concentration, crude product
  8. customis purified by flash chromatography (Hexane/EtOAc
  9. customfollowed by preparative HPLC (0-50% acetonitrile with 0.1% TFA in 21 minutes)
  10. concentrationAfter concentration and free basing

Quellen und Nachweise

ORD-Eintrag
ord-562a9283b3d14dedb5f90d941c4126d1
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08314097B2

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