Acetic Acid → N-((5-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)furan-2-yl)methyl)-2-methoxyethanamine

HRID 1942784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942784
[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[O:18][C:17](C=O)=[CH:16][CH:15]=3)[S:13][C:6]=12.[CH3:28][O:29][CH2:30][CH2:31][NH2:32].[BH-](OC(C)=O)(OC(C)=O)O[C:35](C)=O.[Na+].C(O)(=O)C>ClCCl>[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[O:18][C:17]([CH2:35][NH:32][CH2:31][CH2:30][O:29][CH3:28])=[CH:16][CH:15]=3)[S:13][C:6]=12

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866351855-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)furan-2-carbaldehyde

Produkt 1

HCID 67491421N-((5-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)furan-2-yl)methyl)-2-methoxyethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of 107 (2.00 g, 5.20 mmol), 2-methoxyethylamine (1.954 g, 26.02 mmol), NaBH(OAc)3 (5.52 g, 26.02 mmol) and acetic acid (1.49 ml, 26.02 mmol) in anhydrous dichloromethane was stirred at room temperature under nitrogen for five days. The reaction mixture was then carefully quenched with a saturated solution of NaHCO3 (pH 8-9), and extracted with DCM. The extract was dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound 108 as a yellow-orange sticky oil. The material was used in the next step without further purification. MS (m/z): 444.2 (M+H).

Aufarbeitung

  1. customThe reaction mixture was then carefully quenched with a saturated solution of NaHCO3 (pH 8-9)
  2. extractionextracted with DCM
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-82efbb6641e9423e8d2a54a6b0ee8360
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389541B2

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