Triethylamine → 5-(6-Phenylhex-1-yn-1-yl)quinoline-8-carbaldehyde

HRID 1892451

Reaktionsgleichung

Reaktionsgleichung von HRID 1892451
Br[C:2]1[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:14]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)#[C:15][CH2:16][CH2:17][CH2:18][CH3:19].C(N(CC)CC)C>CN(C=O)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:20]1([CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[C:19][C:2]2[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[N:7]3)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 1369081-Phenyl-1-hexyneHCID 164142435-Bromoquinoline-8-carboxaldehyde

Produkt 1

HCID 866723765-(6-Phenylhex-1-yn-1-yl)quinoline-8-carbaldehydeAusbeute 56,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 812191,3-Bis(diphenylphosphino)propaneKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-8-quinolinecarboxaldehyde (987 mL, 418 mmol), 5-hexyn-1-yl-benzene [CAS 100848-88-2] (1.05 mL, 5.85 mmol), triethylamine (2 mL) and 1,3-bis(diphenylphosphino)propane (dppp, 59 mg) in DMF (10 mL) was heated to 90° C. with stirring for 2 h. After cooling to RT, the reaction mixture was extracted with ether and washed with water and brine, dried over magnesium sulfate and concentrated. Purification by MPLC (35% ethyl acetate in hexanes) gave rise to 1.04 g of Intermediate.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ether
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification by MPLC (35% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-74daaace451143ac84cdf26ee5c8a3fb
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507686B2

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