Furan-3-boronic acid → HCID 86720517, compound

HRID 1054086Notes

Reaction equation

HRID 1054086 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=1.[O:10]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11]1>>[O:10]1[CH:14]=[CH:13][C:12]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=2)=[CH:11]1

Participants

3

Reactant 2

HCID 2734358Furan-3-boronic acidHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 86720517HCID 86720517, compound

Procedure

Synthesized using compound 43c (976 mg, 5.25 mmol) and 3-furanboronic acid (881 mg, 7.87 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (10:1) as eluent. White solid. Yield: 770 mg, 85%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=6.94 (dd, J=1.9, 0.9 Hz, 1H), 7.51-7.55 (m, 1H), 7.58 (dd, J=8.2, 0.6 Hz, 1H), 8.11-8.17 (m, 2H), 9.00 (dd, J=2.2, 0.9 Hz, 1H), 10.06 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=108.5, 120.0, 126.5, 129.6, 136.3, 143.2, 144.4, 152.6, 156.8, 190.1; MS (ESI): m/z=174.26 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (10:1) as eluent

Sources & evidence

ORD record
ord-7a87f6e35fb24f8dbcade7b07bb61d80
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

Loading…