2-Bromo-5-methylpyridine → 5-Methyl-[2,2']bipyridinyl

HRID 1866463노트

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HRID 1866463 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1>C1(C)C=CC=CC=1.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>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[N:3][CH:4]=1

참가 물질

4

반응물 1

HCID 5642162-Bromo-5-methylpyridine

생성물 1

HCID 110738485-Methyl-[2,2']bipyridinyl수율 193%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

A solution of 2-(tributyltin)pyridine (9.20 g, 25 mmol) and 2-bromo-5-methylpyridine (4.3 g, 25 mmol) in toluene was bubbled with argon gas for 10 min. The catalyst Pd(PPh3)4 (0.29 g, 0.25 mmol, 1 mol %) was added and the mixture was refluxed under argon atmosphere for 3 days. Removal of solvent gave an oil that was purified by chromatography over silica gel eluted with CH2Cl2 and then EtOAc. The brown liquid obtained was dried overnight under high vacuum providing 4.1073 g of 5-methyl-[2,2′]bipyridinyl as a brown liquid (24.13 mmol, yield 96.5%). 1H NMR (CDCl3, 300.16 MHz) δ (ppm) 8.66 (ddd, J=4.8, 1.8 & 0.9 Hz, 1H), 8.51 (dt, J=2.9 & 0.7 Hz, 1H), 8.35 (dt, J=8.0 & 1.1 Hz, 1H), 8.28 (d, J=8.1 Hz, 1H), 7.80 (td, J=7.7 & 1.8 Hz, 1H), 7.63 (ddd, J=8.1, 1.5 & 0.7 Hz, 1H), 7.28 (ddd, J=7.5, 4.8 & 1.2 Hz, 1H) and 2.39 (s, 3H). MS (ESI) m/z: 171 (M+1)+ and (2M+23)+.

후처리

  1. temperaturethe mixture was refluxed under argon atmosphere for 3 days
  2. customRemoval of solvent
  3. customgave an oil that
  4. customwas purified by chromatography over silica gel
  5. washeluted with CH2Cl2
  6. customThe brown liquid obtained
  7. customwas dried overnight under high vacuum

출처 및 근거

ORD 기록
ord-55139af07d0a471eba3601930aa2d147
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629375B2

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