Sodium Carbonate → 5-(2-Thiophen-2-yl-phenyl)-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridine

HRID 1877958Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1877958
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:13]2[CH:14]=[N:15][CH:16]=[C:12]2[CH2:11][CH2:10][CH2:9]1.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1B(O)O.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>[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:13]2[CH:14]=[N:15][CH:16]=[C:12]2[CH2:11][CH2:10][CH2:9]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 588271225-(2-Bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Produkt 1

HCID 588271095-(2-Thiophen-2-yl-phenyl)-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-(2-bromophenyl)-5,6,7,8,-tetrahydro-imidazo[1,5-a]pyridine, Example 12D (120 mg, 0.43 mmol) in DME (2 mL) is added thiophene-2-boronic acid (166 mg, 1.3 mmol), aqueous Na2CO3 (2M, 1.0 mL, 2.0 mmol), and Pd(PPh3)4 (20 mg). The reaction mixture is refluxed overnight. The mixture is partitioned between EtOAc and 1M NaOH. The organic layer is washed by sat. NaHCO3, dried and concentrated to give an oil. The crude reaction mixture is subjected to flash chromatography (silica gel) eluting with acetone:hexane to yield the desired compound. MS (ESI) m/z 280 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm 1.58-1.74 (m, 1 H), 1.85-2.01 (m, 2 H), 2.14-2.27 (m, 1 H), 2.74-2.94 (m, 2 H), 5.45 (dd, J=8.6, 5.1 Hz, 1 H), 6.81 (s, 1 H), 7.00-7.05 (m, 2 H), 7.06 (s, 1 H), 7.10 (dd, J=5.3, 3.5 Hz, 1 H), 7.31-7.37 (m, 2 H), 7.39 (dd, J=5.2, 1.1 Hz, 1 H), 7.41-7.46 (m, 1 H).

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed overnight
  2. customThe mixture is partitioned between EtOAc and 1M NaOH
  3. washThe organic layer is washed by sat. NaHCO3
  4. customdried
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe crude reaction mixture
  8. washeluting with acetone

Quellen und Nachweise

ORD-Eintrag
ord-80a219c113a84b77ba7af52c6e9341dc
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314097B2

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