3-Bromo-2-methyl-thieno[3,2-b]pyridine → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(2-methyl-thieno[3,2-b]pyridin-3-yl)-imidazo[1,2-b]pyridazine

HRID 226065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 226065
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[CH3:11].[CH2:12]([CH:14]([C:17]1[C:18]2[N:19]([C:24](I)=[C:25]([CH3:27])[N:26]=2)[N:20]=[C:21]([CH3:23])[CH:22]=1)[CH2:15][CH3:16])[CH3:13]>C1COCC1.[Zn]>[CH2:12]([CH:14]([C:17]1[C:18]2[N:19]([C:24]([C:2]3[C:6]4=[N:7][CH:8]=[CH:9][CH:10]=[C:5]4[S:4][C:3]=3[CH3:11])=[C:25]([CH3:27])[N:26]=2)[N:20]=[C:21]([CH3:23])[CH:22]=1)[CH2:15][CH3:16])[CH3:13]

Komponenten

5

Edukt 2

HCID 577526323-Bromo-2-methyl-thieno[3,2-b]pyridineHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

Produkt 1

HCID 577526838-(1-Ethyl-propyl)-2,6-dimethyl-3-(2-methyl-thieno[3,2-b]pyridin-3-yl)-imidazo[1,2-b]pyridazineAusbeute 9,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

380 mg of 3-Bromo-2-methyl-thieno[3,2-b]pyridine (1.66 mmol) is placed into the vial with 3.56 ml of Reiki Zn, suspension in THF (2.50 mmol) and capped and heated at 100C for 2 h. The excess Zinc is allowed to settle down and the solution is transferred to the vial containing 250 mg of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.72 mmol) and 48 mg of PdCl2(pddf) (0.06 mmol) in 2 ml of dry THF. The vial is capped by Teflon cap and heated at 80C for overnight. The reaction mixture is quenched by sat.NH4Claq. and extracted by CH2Cl2, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane: AcOEt: 2 M NH3 in MeOH=20:4:1) to give 24.2 mg of the title compound. Yield 9.2%. mass spectrum (m/e): 365 (M+1); 1H-NMR (CDCl3): 8.66 (dd, 1H, J=4.7 Hz, 1.4 Hz), 8.16 (dd, 1H, J=8.1 Hz, 1.4 Hz), 7.25 (dd, 1H, J=8.1 Hz, 4.7 Hz), 6.68 (s, 1H), 3.43 (m, 1H), 2.50 (s, 3H), 2.47 (s, 3H), 2.46 (s, 3H), 1.88 (m, 4H), 0.93 (m, 6H) ppm.

Aufarbeitung

  1. customcapped
  2. customcap
  3. customThe reaction mixture is quenched by sat.NH4Claq
  4. extractionand extracted by CH2Cl2
  5. dry with materialdried over Na2SO4
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a5fc92c4d80f4a38af5b6e6f045d67e9
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557103B2

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