N,N,N',N'-Tetramethylethylenediamine → 5-(2-Bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

HRID 923276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 923276
[Br:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][N:5]1[C:9]([CH2:10][CH2:11][CH2:12]Cl)=[CH:8][N:7]=[CH:6]1.CN(CCN(C)C)C.[Li+].CC([N-]C(C)C)C>C1COCC1>[Br:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH:4]1[N:5]2[CH:6]=[N:7][CH:8]=[C:9]2[CH2:10][CH2:11][CH2:12]1

Komponenten

5

Edukt 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 2724682Lithium diisopropylamideHCID 588270851-(2-Bromobenzyl)-5-(3-chloropropyl)-1H-imidazole

Produkt 1

HCID 588271225-(2-Bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a slurry of 1-(2-bromobenzyl)-5-(3-chloropropyl)-1H-imidazole (0.662 g, 2.12 mmol) and TMEDA (0.683 mL, 4.55 mmol) in THF (10 mL) at −78° C. is added LDA (1.8 M in heptane/THF/ethylbenzene, 2.5 mL, 4.5 mmol) and the yellow clear solution is stirred at −78° C. After 3.5 hr, the reaction is quenched by saturated aqueous NH4Cl, and the mixture is partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer is washed with brine, dried and concentrated to give an oil, which is subjected to flash chromatography (silica gel) eluting with MeOH:CH2Cl2 to yield the desired compound. MS (ESI) m/z 277 (M+H).

Aufarbeitung

  1. customthe reaction is quenched by saturated aqueous NH4Cl
  2. customthe mixture is partitioned between EtOAc and saturated aqueous NaHCO3
  3. washThe organic layer is washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give an oil, which
  7. washeluting with MeOH

Quellen und Nachweise

ORD-Eintrag
ord-4dbe04ba765245c0b8f02b1b0de51b16
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278969B2

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