5-Methylpyridine-3-boronic acid → 5-((5-Methylpyridin-3-yl)methyl)-2-phenylpyridine

HRID 1054122Notes

Reaction equation

HRID 1054122 reaction equation
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:17]=[C:18](B(O)O)[CH:19]=[N:20][CH:21]=1>>[CH3:15][C:16]1[CH:17]=[C:18]([CH2:2][C:3]2[CH:4]=[CH:5][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:7][CH:8]=2)[CH:19]=[N:20][CH:21]=1

Participants

3

Reactant 2

HCID 27627085-Methylpyridine-3-boronic acidHCID 159459965-(Bromomethyl)-2-phenylpyridine

Product 1

HCID 573300865-((5-Methylpyridin-3-yl)methyl)-2-phenylpyridine

Procedure

Synthesized using compound 61a (70 mg, 0.28 mmol) and 5-methylpyridine-3-boronic acid (58 mg, 0.42 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel 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: 56 mg, 77%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=2.30 (d, J=0.6 Hz, 3H), 3.98 (s, 2H), 7.28-7.32 (m, 1H), 7.38-7.44 (m, 1H), 7.44-7.55 (m, 3H), 7.67 (dd, J=8.0, 0.8 Hz, 1H), 7.96-8.01 (m, 2H), 8.36 (d, J=1.6 Hz, 1H), 8.33 (d, J=1.6 Hz, 1H), 8.58 (dd, J=1.6, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=18.3, 35.7, 120.4, 126.7, 128.7, 128.9, 133.1, 133.8, 134.8, 136.8, 137.0, 139.0, 147.2, 148.6, 149.8, 155.8; (ESI): m/z=260.84 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel ethyl acetate as eluent
  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

Sources & evidence

ORD record
ord-11d40bbcffac44f4bda51789adab3166
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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