Dichloromethane → [5-(9H-carbazol-4-yl)pyridin-2-yl]methanol

HRID 1877456

反応式

HRID 1877456 の反応式
[OH:1][CH2:2][C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].ClCCl.FC(F)(F)S(O[C:27]1[C:39]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][C:31]=2[CH:30]=[CH:29][CH:28]=1)(=O)=O>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:30]1[C:31]2[NH:32][C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:39]=2[C:27]([C:6]2[CH:5]=[CH:4][C:3]([CH2:2][OH:1])=[N:8][CH:7]=2)=[CH:28][CH:29]=1

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 441182556-(Hydroxymethyl)pyridine-3-boronic acidHCID 583383234-Trifluoromethanesulphonyloxycarbazole

生成物 1

HCID 67308755[5-(9H-carbazol-4-yl)pyridin-2-yl]methanol収率 47.4%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

0.54 g of [6-(hydroxymethyl)pyridin-3-yl]boronic acid, 3.3 g of caesium carbonate and 93 mg of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride as a complex with dichloromethane (1/1) [PdCl2(dppO'CH2Cl2] are successively added, under argon, to a solution of 0.8 g of 4-trifluoromethanesulphonyloxycarbazole, obtained in stage 1 of Example 1, in a mixture of 37 ml of dioxane and 12 ml of water. The reaction mixture is refluxed for 5 hours, cooled to ambient temperature and concentrated under reduced pressure. The residue is subsequently taken up with a mixture of dichloromethane and ethyl acetate, treated with carbon black, filtered through celite and concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a mixture of cyclohexane and ethyl acetate (55/45 by volume), so as to give 0.33 g of [5-(9H-carbazol-4-yl)pyridin-2-yl]methanol in the form of a colourless oil, the characteristics of which are the following:

後処理

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue is subsequently taken up with a mixture of dichloromethane and ethyl acetate
  4. additiontreated with carbon black
  5. filtrationfiltered through celite and
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel chromatography, elution
  8. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (55/45 by volume)

出典と根拠

ORDレコード
ord-07590bc6edc9417d90f7d425d358aa4b
出典データセット
uspto-grants-2012_11
特許番号
US08309721B2

関連ノート

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