Potassium Phosphate, Tribasic → 3-Benzyl-5-nitropyridine

HRID 2367682

反応式

HRID 2367682 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[CH2:11](B1OC(C)(C)C(C)(C)O1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:11]([C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 27628983-Bromo-5-nitropyridineHCID 38649642-Benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 735549143-Benzyl-5-nitropyridine収率 37.2%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 3-bromo-5-nitropyridine (LXXVII) (295 mg, 1.45 mmol) in dioxane (14 mL) was added 2-benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (LXXVIII) (420 μL, 1.89 mmol), PdCl2(dppf)2, (120 mg, 0.15 mmol) and 2M aqueous K3PO4 (2.2 mL, 4.36 mmol). The reaction was microwaved at 90° C. for 2 h. The reaction was cooled and the organic phase was separated, dried over MgSO4 and evaporated under vacuum. The residue was purified by silica gel column chromatography (100% hexane 6:94 EtOAc:hexane) to give 3-benzyl-5-nitropyridine (LXXIX) as brown oil (117 mg, 0.54 mmol, 37% yield). 1H NMR (DMSO-d6) δ ppm 4.16 (s, 2H), 7.21-7.25 (m, 1H), 7.31-7.33 (m, 4H), 8.45-8.46 (m, 1H), 8.93 (d, J=2 Hz, 1H), 9.21 (d, J=3 Hz, 1H); ESIMS found for C12H10N2O2 m/z 215 (M+H).

後処理

  1. customThe reaction was microwaved at 90° C. for 2 h
  2. temperatureThe reaction was cooled
  3. customthe organic phase was separated
  4. dry with materialdried over MgSO4
  5. customevaporated under vacuum
  6. customThe residue was purified by silica gel column chromatography (100% hexane 6:94 EtOAc:hexane)

出典と根拠

ORDレコード
ord-3f2a847532cb4b7ca30ab5f32ea63aba
出典データセット
uspto-grants-2014_04
特許番号
US08697887B2

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