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

HRID 573599
ノート
印刷プレビュー

反応式

HRID 573599 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 634876Binap, (A+-)-触媒
HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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),

後処理

  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

出典と根拠

ORDレコード
ord-3fa8a146c40346b68a0a204e0b03e7fc
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09029545B2

反応ノート

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