1-Pentanethiol → HCID 57548072, Verbindung

HRID 660190

Reaktionsgleichung

Reaktionsgleichung von HRID 660190
Br[C:2]1[N:6]=[CH:5][N:4]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.[CH2:21]([SH:26])[CH2:22][CH2:23][CH2:24][CH3:25].C([O-])([O-])=O.[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C(C)=CC=CC=1>[CH2:21]([S:26][C:2]1[N:6]=[CH:5][N:4]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:22][CH2:23][CH2:24][CH3:25]

Komponenten

8

Edukt 4

HCID 80671-PentanethiolHCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 575480803-[5-bromo-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-yl]-pyridine

Produkt 1

HCID 57548072HCID 57548072, VerbindungAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 7237O-XyleneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a degassed solution of xylene (100 ml) containing 73 (1.82 g, 5.16 mmol), were added 1.25 eq (0.80 ml) of pentane-1-thiol and 1.25 eq of K2CO3 (0.8 g). The resulting mixture was stirred for another 2 hours under N2. Successively were added 10 mol % of Pd2(dba)3 (470 mg) and 20 mol % mmol Xantphos (600 mg). After the addition, the resulting solution was stirred for 18 hours at 130° C. under N2. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with a saturated NaHCO3 solution, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by flash chromatography (diethyl ether followed by ethyl acetate) to afford 3-[5-pentylsulfanyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-yl]-pyridine (74A) as an oil (530 mg, 30%) and starting material (73, 380 mg, 21%), 1H-NMR (400 MHz, CDCl3): δ 9.38 (d, J=2 Hz, 1H), 8.53 (dd, J=5 Hz, 2 Hz, 1H), 8.42 (dt, J=8 Hz, 2 Hz, 1H), 7.82 (s, 1H), 7.35-7.30 (m, 1H), 5.43 (s, 2H), 3.59-3.54 (m, 2H), 2.66 (t, J=7 Hz, 2H), 1.47-1.38 (m, 2H), 1.28-1.10 (m, 4H), 0.96-0.89 (m, 2H), 0.80 (t, J=7 Hz, 3H), 0.0 (s, 9H).

Aufarbeitung

  1. additionAfter the addition
  2. stirringthe resulting solution was stirred for 18 hours at 130° C. under N2
  3. washwashed with a saturated NaHCO3 solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (diethyl ether followed by ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ad11e472c0a5482b892bd9d8b4c40c29
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084473B2

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