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

HRID 1952456ノート

反応式

HRID 1952456 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-046bb6aa52ef42a4866557b28e06be7f
出典データセット
uspto-grants-2013_03
特許番号
US08404846B2

反応ノート

読み込み中…