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

HRID 416214

반응식

HRID 416214 반응식
[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

참가 물질

5

반응물 2

HCID 10340Sodium CarbonateHCID 3008092-Amino-6-bromopyridine

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5346d089d8c14d568568d36a867b08cc
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088805B2

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