Nitrogen → N-[3-(2,2-dipyridin-3-ylethyl)pyridin-2-yl]benzene-1,2-diamine

HRID 1686070노트

반응식

HRID 1686070 반응식
Cl[C:2]1[C:7]([CH2:8][CH:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:22]1([NH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:28].CC(C)([O-])C.[Na+].N#N>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].[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2]>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:8][C:7]2[C:2]([NH:28][C:23]3[C:22]([NH2:29])=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=1

참가 물질

8

반응물 4

HCID 947NitrogenHCID 7243O-PhenylenediamineHCID 23676156Sodium t-butoxideHCID 866343192-Chloro-3-(2,2-dipyridin-3-ylethyl)pyridine

생성물 1

HCID 67264573N-[3-(2,2-dipyridin-3-ylethyl)pyridin-2-yl]benzene-1,2-diamine

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 152416121,1`-Bis(diphenylphosphino)ferrocene촉매HCID 1140Toluene용매

실험 절차

To a solution of 2-chloro-3-(2,2-dipyridin-3-ylethyl)pyridine in 160 mL toluene was added phenylenediamine (8.41 g), tris(dibenzylideneacetone)-dipalladium(0) (356 mg), 1,1-bis(diphenylphosphino)ferrocene (431 mg), and sodium tert-butoxide (2.24 g) under N2. The reaction was heated at 100 C under a stream of N2 for 14 h, then partitioned between saturated aqueous sodium bicarbonate and CH2Cl2. The aqueous solution was extracted with CH2Cl2 (3×), and the combined organic solutions were dried (Na2SO4) and concentrated. To the resulting black residue were added CH2Cl2 and hexane, and the precipitated solid was filtered off (washing with 1:1 CH2Cl2:hexane, followed by toluene). The filtrate was concentrated and purified by flash chromatography to give 4.1 g of N-[3-(2,2-dipyridin-3-ylethyl)pyridin-2-yl]benzene-1,2-diamine as a grey solid.

후처리

  1. custompartitioned between saturated aqueous sodium bicarbonate and CH2Cl2
  2. extractionThe aqueous solution was extracted with CH2Cl2 (3×)
  3. dry with materialthe combined organic solutions were dried (Na2SO4)
  4. concentrationconcentrated
  5. additionTo the resulting black residue were added CH2Cl2 and hexane
  6. filtrationthe precipitated solid was filtered off
  7. wash(washing with 1:1 CH2Cl2:hexane, followed by toluene)
  8. concentrationThe filtrate was concentrated
  9. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-1dae641de9d940a6b0110b16ef91b239
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148535B2

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