2-Methoxyethylamine → N-((6-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)-2-methoxyethanamine

HRID 84376

Reaktionsgleichung

Reaktionsgleichung von HRID 84376
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][N:15]=3)[S:13][C:6]=12.[CH3:29][O:30][CH2:31][CH2:32][NH2:33].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]=[CH:16][C:17]([CH2:18][NH:33][CH2:32][CH2:31][O:30][CH3:29])=[CH:20][CH:21]=3)[S:13][C:6]=12

Komponenten

5

Edukt 3

HCID 80182-MethoxyethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 594576666-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)nicotinaldehyde

Produkt 1

HCID 57919574N-((6-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)-2-methoxyethanamineAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 123 (700 mg, 1.77 mmol) and 2-methoxyethanamine (185 □L, 160 mg, 2.12 mmol) in DCM (7 mL) was stirred at room temperature for 10 min. It was then treated with NaBH(OAc)3 (526 mg, 2.48 mmol) and stirred at room temperature overnight. The reaction mixture was diluted with DCM (20 mL) and washed with saturated NaHCO3 solution (20 mL). The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash chromatography using the gradient 4-8% MeOH/DCM to afford 124 (675 mg, 65% yield). MS (m/z): 455.2 (M+H).

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. washwashed with saturated NaHCO3 solution (20 mL)
  3. customThe organic phase was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-174a6c6b18bf4284aff7b57bcc3ec5fc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846927B2

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