Diisopropylamine → 5-Bromo-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine

HRID 1916530

反応式

HRID 1916530 の反応式
[CH2:1]([C:5]1[CH:16]=[CH:15][C:8]([CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:7][CH:6]=1)[CH2:2][C:3]#[CH:4].Br[C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][N:19]=1.C(NC(C)C)(C)C>C1COCC1.O.[Cu]I>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([C:4]#[C:3][CH2:2][CH2:1][C:5]2[CH:16]=[CH:15][C:8]([CH2:9][N:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=2)=[N:19][CH:20]=1

参加物

7

反応物 3

HCID 7912DiisopropylamineHCID 693532,5-DibromopyridineHCID 859698431-(4-But-3-ynyl-benzyl)-pyrrolidine

生成物 1

HCID 690713915-Bromo-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

A mixture of 200 mg (0.94 mmol) 1-(4-but-3-ynyl-benzyl)-pyrrolidine, 222 mg (0.94 mmol) 2,5-dibromopyridine, 13.2 mg (0.02 mmol) tetrakis-triphenylphosphane-palladium, 3.6 mg (0.02 mmol) CuI and 0.27 mL diisopropylamine in 10 mL THF is heated for 4 h at 40° C. under an argon atmosphere. The reaction mixture is diluted with water, exhaustively extracted with EtOAc, the organic phase is washed with saturated, aqueous NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5).

後処理

  1. extractionexhaustively extracted with EtOAc
  2. washthe organic phase is washed with saturated, aqueous NaCl solution
  3. dry with materialdried over Na2SO4
  4. customis purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5)

出典と根拠

ORDレコード
ord-e13c917bb04b4f3c8bd29402a92662eb
出典データセット
uspto-grants-2013_12
特許番号
US08618132B2

関連ノート

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