2,6-Dibromopyridine → HCID 86641856, 화합물

HRID 572206

반응식

HRID 572206 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH2:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16](Br)[N:15]=1.C1(P(C2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=C(C3C4C(=CC=CC=4)C=CC=3)C3C(C=2)=CC=CC=3)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:13][C:14]1[N:15]=[C:16]([NH:12][C@H:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH3:11])[CH:17]=[CH:18][CH:19]=1

참가 물질

7

반응물 4

HCID 122742,6-DibromopyridineHCID 11292459HCID 11292459, 화합물HCID 18630801Bis(diphenylphosphino)-1,1'-binaphthylHCID 23676156Sodium t-butoxide

생성물 1

HCID 86641856HCID 86641856, 화합물수율 33%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A mixture of (1S)-1-(3-nitrophenyl)ethanamine (365 mg, 2.2 mmol), 2,6-dibromopyridine (474 mg, 2 mmol), tris(dibenzylidene)dipalladium(0) (92 mg, 0.1 mmol), (+/−)-bis(diphenyphosphino)-1,1′-binaphthalene (125 mg, 0.2 mmol) and sodium tert-butoxide (270 mg, 2.8 mmol) in anhydrous toluene (4 mL) was heated at 80° C. for 17 hours. The mixture was cooled, diluted with ethyl acetate (50 mL), washed successively with saturated aqueous sodium hydrogen carbonate (3×30 mL) and brine (30 mL), dried (Na2SO4) and concentrated under reduced pressure to give a black oil which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give 6-bromo-N-[(1S)-1-(3-nitrophenyl)ethyl]pyridin-2-amine (210 mg, 33%) and the di-addition product (205 mg, 50%) both as yellow oils.

후처리

  1. temperatureThe mixture was cooled
  2. washwashed successively with saturated aqueous sodium hydrogen carbonate (3×30 mL) and brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give a black oil which
  6. customwas purified by flash chromatography (silica, ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-669d641cd5904fd7b163a83c97b03946
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029386B2

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