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Pyrrolidine → 3-Bromo-5-(pyrrolidin-1-yl)pyridine

HRID 573599
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인쇄 미리보기

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HRID 573599 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.CC(C)([O-])C.[Na+].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 31268PyrrolidineHCID 693693,5-DibromopyridineHCID 23676156Sodium t-butoxide

생성물 1

HCID 467395273-Bromo-5-(pyrrolidin-1-yl)pyridine수율 75.9%

시약·촉매·용매 3

HCID 634876Binap, (A+-)-촉매
HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 1140Toluene용매

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온도
100 °C

실험 절차

To a solution of 3,5-dibromopyridine (5.5 g, 23.22 mmol) in toluene (100 mL) was added BINAP (0.840 g, 1.350 mmol), Pd2(dba)3 (0.412 g, 0.45 mmol), sodium tert-butoxide (6.49 g, 67.5 mmol) and pyrrolidine (1.86 mL, 22.50 mmol). The reaction mixture was degassed (N2, 10 min) and then heated at 100° C. for 2 h. The reaction mixture was cooled to RT and filtered through celite. The filtrate was evaporated and the residue purified by silica gel chromatography, eluting with a gradient of 0-30% ethyl acetate in cyclohexane, to afford the title compound (3.88 g). LCMS (A) m/z: 227/229 [M+1]+, Rt 0.87 min (acidic),

후처리

  1. customThe reaction mixture was degassed (N2, 10 min)
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through celite
  4. customThe filtrate was evaporated
  5. customthe residue purified by silica gel chromatography
  6. washeluting with a gradient of 0-30% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-3fa8a146c40346b68a0a204e0b03e7fc
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09029545B2

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