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

HRID 1866463ノート

反応式

HRID 1866463 の反応式
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

参加物

4

反応物 1

HCID 5642162-Bromo-5-methylpyridine

生成物 1

HCID 110738485-Methyl-[2,2']bipyridinyl収率 193%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-55139af07d0a471eba3601930aa2d147
出典データセット
uspto-grants-2009_12
特許番号
US07629375B2

反応ノート

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