N-Methyl-3-pyridinamine → 3-(2,2-dipyridin-3-ylethyl)-N-methyl-N-pyridin-3-ylpyridin-2-amine

HRID 1686072

反応式

HRID 1686072 の反応式
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.[CH3:22][NH:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.CC(C)([O-])C.[Na+]>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]([N:23]([CH3:22])[C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=1

参加物

7

反応物 3

HCID 140376N-Methyl-3-pyridinamineHCID 23676156Sodium t-butoxideHCID 86634319HCID 86634319、化合物

生成物 1

HCID 166623133-(2,2-dipyridin-3-ylethyl)-N-methyl-N-pyridin-3-ylpyridin-2-amine収率 38%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 152416121,1`-Bis(diphenylphosphino)ferrocene触媒HCID 1140Toluene溶媒

実験手順

To a solution of 2-chloro-3-(2,2-dipyridin-3-ylethyl)pyridine (1.54 g) and 3-(methylamino)pyridine (732 mg) in 30 mL toluene were added tris(dibenzylideneacetone)-dipalladium(0) (119 mg), 1,1-bis(diphenylphosphino)ferrocene (144 mg), and sodium tert-butoxide (651 mg). The reaction was heated at 100 C under a stream of Ar for 5 h. The reaction was cooled to room temp, 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. Flash chromatography gave a dark semi-solid which was purified again by reverse phase HPLC to provide 727 mg of 3-(2,2-dipyridin-3-ylethyl)-N-methyl-N-pyridin-3-ylpyridin-2-amine. 1H NMR (500 MHz, CDCl3): δ 8.44 (m, 2H), 8.35-8.34 (m, 3H), 8.15 (d, J=4.2 Hz, 1H), 8.04 (d, J=2.2 Hz, 1H), 7.42 (dd, J=7.6, 1.7 Hz, 1H), 7.36-7.34 (m, 2H), 7.19-7.12 (m, 3H), 7.03 (dd, J=7.6, 4.9 Hz), 6.96-6.94 (m, 1H), 4.26 (t, J=7.8 Hz, 1H), 3.25 (s, 3H), 3.16 (d, J=7.8 Hz, 2H).

後処理

  1. temperatureThe reaction was heated at 100 C under a stream of Ar for 5 h
  2. custompartitioned between saturated aqueous sodium bicarbonate and CH2Cl2
  3. extractionThe aqueous solution was extracted with CH2Cl2 (3×)
  4. dry with materialthe combined organic solutions were dried (Na2SO4)
  5. concentrationconcentrated
  6. customFlash chromatography gave a dark semi-solid which
  7. customwas purified again by reverse phase HPLC

出典と根拠

ORDレコード
ord-a811b995e14648538d298740c4c24c1c
出典データセット
uspto-grants-2012_04
特許番号
US08148535B2

関連ノート

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