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

HRID 1507100

반응식

HRID 1507100 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 735549143-Benzyl-5-nitropyridine수율 37.2%

시약·촉매·용매 2

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7871ba976c52439798286fa590102b74
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221793B2

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