4-Methylpyridine-3-Boronic Acid → 5-((4-Methylpyridin-3-yl)methyl)-2-phenylpyridine

HRID 1054121ノート

反応式

HRID 1054121 の反応式
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:7][CH:8]=1.[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1B(O)O>>[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:7][CH:8]=1

参加物

3

反応物 2

HCID 27627114-Methylpyridine-3-Boronic AcidHCID 159459965-(Bromomethyl)-2-phenylpyridine

生成物 1

HCID 573300855-((4-Methylpyridin-3-yl)methyl)-2-phenylpyridine

実験手順

Synthesized using compound 61a (100 mg, 0.40 mmol) and 4-methylpyridine-3-boronic acid (83 mg, 0.61 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using ethyl acetate as eluent. After flash chromatography the product was solved in ethyl acetate and a few drops of conc. HCl and water were added. After stirring for 30 minutes the phases were separated and water phase was neutralized with aqueous Na2CO3-solution (2M). After extraction with ethyl acetate and drying over MgSO4 the solvent was removed under vacuum. Light yellow solid. Yield: 54 mg, 52%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=2.22-2.29 (m, 3H), 4.02 (s, 2H), 7.11 (d, J=5.0 Hz, 1H), 7.37-7.51 (m, 4H), 7.64 (dd, J=8.2, 0.6 Hz, 1H), 7.95-8.01 (m, 2H), 8.38-8.46 (m, 2H), 8.52-8.57 (m, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=19.3, 33.8, 120.5, 125.7, 126.9, 129.0, 129.1, 133.2, 133.8, 136.8, 139.2, 146.1, 148.7, 149.9, 150.7, 155.9; (ESI): m/z=260.85 [M+H]+.

後処理

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona few drops of conc. HCl and water were added
  4. customwere separated
  5. extractionAfter extraction with ethyl acetate
  6. dry with materialdrying over MgSO4 the solvent
  7. customwas removed under vacuum

出典と根拠

ORDレコード
ord-69383aac9eca41ce81d34fc3f30666e9
出典データセット
uspto-grants-2016_07
特許番号
US09394290B2

反応ノート

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