Furan-3-boronic acid → HCID 11484311, compound

HRID 2242397Notes

Reaction equation

HRID 2242397 reaction equation
Br[C:2]1[C:11]2[O:10][CH2:9][C:8]3[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:7]=3[C:6]=2[CH:5]=[C:4]2[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:3]=12.[O:22]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23]1>CN(C=O)C.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>[O:22]1[CH:26]=[CH:25][C:24]([C:2]2[C:11]3[O:10][CH2:9][C:8]4[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:7]=4[C:6]=3[CH:5]=[C:4]3[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:3]=23)=[CH:23]1

Participants

5

Reactant 2

HCID 2734358Furan-3-boronic acidHCID 11416607HCID 11416607, compound

Product 1

HCID 11484311HCID 11484311, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 7-bromo-5H-dibenzo[c,g]chromene-3,9-diol (342.mg, 1.0 mmol), furan-3-boronic acid (224 mg, 2 mmols) and tetrakis(triphenylphosphine)palladium(0) (116 mg, 0.1 mmoles) in DMF (20 ml) is heated at 120° C. with stirring for 4 h. The mixture was filtered through celite, extracted with ethyl acetate (×3), washed with brine, dried over sodium sulfate, filtered, stripped of solvent and purified by silica column chromatography (18%-25% ethyl acetate-hexane) to yield 200 mg (61%) of the title compound as a yellowish solid: mp 216-218° C.; 1H NMR (DMSO-d6): δ 5.00 (2H, s), 6.66 (2H, m), 6.84 (1H, dd, J=8.45 Hz, J=2.35 Hz), 6.93 (1H, dd, J=8.77 Hz, J=2.35 Hz), 7.04 (1H, d, J=2.17 Hz), 7.76 (1H, d, J=8.83 Hz), 7.80-7.85 (3H, m), 8.16 (1H, s), 9.61 (1H, s), 9.71 (1H, s); MS (ESI) m/z 329 (M−H)−, 331 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through celite
  2. extractionextracted with ethyl acetate (×3)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. custompurified by silica column chromatography (18%-25% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-75c38a35f53f43d594cd78d89ae20f05
Source dataset
uspto-grants-2010_03
Patent number
US07671084B2

Reaction notes

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