Tetrahydrofuran → tert-Butyl [5-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)pyridin-3-yl]carbamate

HRID 541885

反応式

HRID 541885 の反応式
I[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].O1CCCC1.[C:24]([C:26]1[CH:27]=[C:28]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH:29]=[N:30][CH:31]=1)#[CH:25]>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CC)CC)C>[C:14]([O:13][C:12]([NH:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[C:25]#[C:24][C:26]1[CH:27]=[C:28]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:37])([CH3:36])[CH3:38])[CH:29]=[N:30][CH:31]=1)=[O:18])([CH3:17])([CH3:16])[CH3:15]

参加物

7

反応物 3

HCID 8028TetrahydrofuranHCID 7098713Tert-butyl 4-nitro-2-iodophenylcarbamateHCID 57962286Tert-butyl (5-ethynylpyridin-3-yl)carbamate

生成物 1

HCID 57961805tert-Butyl [5-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)pyridin-3-yl]carbamate収率 85.9%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

実験手順

Into the reaction flask was added tert-butyl (2-iodo-4-nitrophenyl)carbamate (1.5 g, 4.1 mmol) and copper(I) iodide (0.031 g, 0.16 mmol), bis(triphenylphosphine)palladium(II) chloride (0.12 g, 0.16 mmol), tetrahydrofuran (10 mL), and triethylamine (0.63 mL). The mixture was stirred under bubbling N2 for 5 min, and tert-butyl (5-ethynylpyridin-3-yl)carbamate (0.90 g, 4.1 mmol) was then added. The reaction mixture was stirred at 65° C. for 1 h. After concentration, the residue was diluted with EtOAc and water. The aqueous layer was extracted again with EtOAc. The organic layers were combined and dried over Na2SO4. After filtration and concentration, the crude was purified by silica gel column chromatography to give the desired product (1.6 g, 85%). LCMS for C23H27N4O6 (M+H)+: m/z=455.1.

後処理

  1. stirringThe reaction mixture was stirred at 65° C. for 1 h
  2. concentrationAfter concentration
  3. additionthe residue was diluted with EtOAc and water
  4. extractionThe aqueous layer was extracted again with EtOAc
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe crude was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-35cd0205c64f46ebb284da88f40a808b
出典データセット
uspto-grants-2014_10
特許番号
US08871753B2

関連ノート

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