Tetrahydrofuran → Methyl 6-iodo-5-(2-(thiophen-3-yl)ethoxy)nicotinate

HRID 84585

反応式

HRID 84585 の反応式
[OH:1][C:2]1[C:3]([I:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O-:9])=[O:8].[S:12]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18]O)=[CH:13]1.[C:20]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[I:11][C:3]1[C:2]([O:1][CH2:18][CH2:17][C:14]2[CH:15]=[CH:16][S:12][CH:13]=2)=[CH:10][C:6]([C:7]([O:9][CH3:20])=[O:8])=[CH:5][N:4]=1

参加物

6

反応物 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 83731Thiophene-3-ethanolHCID 178524761HCID 178524761、化合物

生成物 1

HCID 57900415Methyl 6-iodo-5-(2-(thiophen-3-yl)ethoxy)nicotinate収率 93.2%

実験手順

To a solution containing 5-hydroxy-6-iodonicotinate (3.70 g, 13.3 mmol;), 2-(3-thienyl)ethanol (1.90 mL, 17.2 mmol), and triphenylphosphine (4.52 g, 17.2 mmol;) in tetrahydrofuran (73.3 mL, 903 mmol;) was added Diisopropyl azodicarboxylate (3.39 mL, 17.2 mmol;) dropwise. The reaction mixture was stirred at RT o/n. The reaction mixture was concentrated and purified by flash chromatography EtOAc/Hex (0-100%) (eluted at 30%) to give methyl 6-iodo-5-(2-(thiophen-3-yl)ethoxy)nicotinate (93.2% yield). MS: (ESI+) 390.1

後処理

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash chromatography EtOAc/Hex (0-100%) (eluted at 30%)

出典と根拠

ORDレコード
ord-2043bf8acd764dada998be60618b26bc
出典データセット
uspto-grants-2014_09
特許番号
US08846762B2

関連ノート

読み込み中…