Water → 2-Amino-3-nitro-5-pyridin-3-yl-pyridine

HRID 722071

反応式

HRID 722071 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH2:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20](Br)=[CH:19][N:18]=1.O>O1CCOCC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.Cl[Pd]Cl>[NH2:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:19][N:18]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 1388782-Amino-5-bromo-3-nitropyridineHCID 27343783-Pyridinylboronic acid

生成物 1

HCID 218827122-Amino-3-nitro-5-pyridin-3-yl-pyridine

試薬・触媒・溶媒 2

HCID 11050900Dichlorobis(tricyclohexylphosphine)pallium (II)触媒HCID 312751,4-Dioxane溶媒

実験手順

0.21 g of dichlorobis(tricyclohexylphosphine)palladium, 0.66 g of 3-pyridyl-boronic acid and 14 ml of a 2N sodium carbonate solution are added to a solution of 1.02 g of 2-amino-5-bromo-3-nitropyridine in 40 ml of degassed dioxane. The mixture is heated to reflux under N2 for 28 hours and, after cooling and addition of water, extracted three times with dichloromethane. The combined organic phases are dried over sodium sulfate, concentrated and the residue is crystallized from ethyl acetate. This gives 0.58 g of the title compound of m.p. 226–228° C. The mass spectrum shows the molecular peak MH+ at 217.2 Da.

後処理

  1. temperatureThe mixture is heated
  2. temperatureto reflux under N2 for 28 hours
  3. temperatureafter cooling
  4. extractionextracted three times with dichloromethane
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue is crystallized from ethyl acetate

出典と根拠

ORDレコード
ord-a9fbc260b4fa49dfacc3a3a1be196a4f
出典データセット
uspto-grants-2006_11
特許番号
US07138399B2

関連ノート

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