Isoquinoline-4-boronic acid → 4-((6-Phenylpyridin-3-yl)methyl)isoquinoline

HRID 1054106Notes

Reaction equation

HRID 1054106 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.[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](B(O)O)=[CH:17][N:16]=1>>[C:9]1([C:6]2[N:7]=[CH:8][C:3]([CH2:2][C:18]3[C:19]4[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:15]=[N:16][CH:17]=3)=[CH:4][CH:5]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 3761204Isoquinoline-4-boronic acidHCID 159459965-(Bromomethyl)-2-phenylpyridine

Product 1

HCID 573300114-((6-Phenylpyridin-3-yl)methyl)isoquinoline

Procedure

Synthesized using compound 61a (109 mg, 0.44 mmol) and isoquinolin-4-ylboronic acid (114 mg, 0.66 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (3:1) 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. Beige solid. Yield: 20 mg, 19%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=4.43 (s, 2H), 7.37-7.54 (m, 4H), 7.59-7.65 (m, 2H), 7.65-7.75 (m, 1H), 7.89-8.07 (m, 4H), 8.48 (s, 1H), 8.65-8.70 (m, 1H), 9.23 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=33.2, 120.3, 123.1, 126.7, 127.2, 128.4, 128.6, 128.6, 128.7, 128.9, 130.7, 133.6, 134.6, 136.7, 139.0, 143.7, 149.7, 152.3, 155.7; (ESI): m/z=296.95 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-26823f94712b4e15988704431b7fff6a
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

Loading…