Sodium Carbonate → [2,3'-Bipyridin]-6-amine

HRID 416214

反応式

HRID 416214 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:3]1[C:2]([NH2:1])=[CH:7][CH:6]=[CH:5][C:4]=1[C:7]1[CH:2]=[N:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 2

HCID 10340Sodium CarbonateHCID 3008092-Amino-6-bromopyridine

生成物 1

HCID 11586359[2,3'-Bipyridin]-6-amine収率 153.7%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

To a stirred degassed suspension of a mixture of 2-amino-6-bromopyridine (5.38 g, 31.09 mmol), 2,4,6-(3-pyridinyl)-cyclotriboroxane (3.80 g, 12.07 mmol) and aqueous Na2CO3 (100 mL, 0.4M) in acetonitrile (100 mL) at room temperature Pd(PPh3)4 (1.70 g, 1.47 mmol) was added. The reaction mixture was heated at 95° for 1 to 2 days under nitrogen, cooled to the room temperature and filtered. The filtrate was concentrated purified by flash chromatography on silica gel (MeOH/CH2Cl2: 5/95→10/90 plus a few drops of NH4OH) and co-precipitated with a mixture of AcOEt/CH2Cl2/hexane to afford the title compound 11 (4.091 g, 23.90 mmol, 77% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.16 (dd, J=2.2, 0.8 Hz, 1H), 8.57 (dd, J=4.7, 1.6 Hz 1H), 8.33-8.28 (m, 1H), 7.54-7.44 (m, 2H), 7.14 (dd, J=7.3, 0.5 Hz, 1H), 6.49 (dd, J=8.2, 0.4 Hz 1H), 6.12 (bs, 2H).

後処理

  1. customTo a stirred degassed
  2. additionwas added
  3. temperatureThe reaction mixture was heated at 95° for 1 to 2 days under nitrogen
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash chromatography on silica gel (MeOH/CH2Cl2: 5/95→10/90 plus a few drops of NH4OH) and co-precipitated with a mixture of AcOEt/CH2Cl2/hexane

出典と根拠

ORDレコード
ord-5346d089d8c14d568568d36a867b08cc
出典データセット
uspto-grants-2012_01
特許番号
US08088805B2

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