1,3-Propanediol → HCID 9840796, compound

HRID 2086067Notes

Reaction equation

HRID 2086067 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:12]=3)[C:5]2=[N:6][CH:7]=1.[O:23]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24]1.C(O)CCO>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].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:23]1[CH:27]=[CH:26][C:25]([C:2]2[CH:3]=[C:4]3[N:10]=[CH:9][N:8]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([C:17]5[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=5)[CH:12]=4)[C:5]3=[N:6][CH:7]=2)=[CH:24]1

Participants

7

Reactant 3

HCID 104421,3-PropanediolHCID 2734358Furan-3-boronic acidHCID 11152319HCID 11152319, compound

Product 1

HCID 9840796HCID 9840796, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 6-bromo-3-[3-(pyridin-3-yl)phenyl]-3H-imidazo[4,5-b]pyridine (351 mg, 1 mmol), 3-furanboronic acid (168 mg, 1.5 mmol), tetrakis(triphenylphosphine)palladium(0) (25 mg) and 1,3-propanediol (360 μl, 5 mmol) in 1,2-dimethoxyethane (6 ml) and 2M sodium carbonate solution (3 ml) was heated at 90° C. for 16 hours. The reaction was cooled and partitioned between ethyl acetate (50 ml) and water (50 ml). The organic layer was then washed with brine, dried over anhydrous sodium sulphate, filtered and pre-adsorbed on to silica. Purification by silica gel chromatography eluting with dichloromethane/methanol/0.88 NH3 (95:4.5:0.5) furnished the title compound as a cream-coloured solid (208 mg, 62%), m.p. 191-192° C. (Found C, 73.13; H, 3.93; N, 16.01. C21H14N4O. 0.4H2O requires C, 72.99; H, 4.32; N, 16.21); δH (400 MHz, d6-DMSO) 7.17 (1H, s), 7.54-7.57 (1H, m), 7.74-7.85 (3H, m), 8.09 (1H, d, J 8), 8.22 (1H, d, J 8), 8.35 (2H, d, J 6), 8.50 (1H, s), 8.63 (1H, d, J 4), 8.80 (1H, s), 9.05 (1H, s), 9.07 (1H, s); m/z (ES+) 339 (M++H).

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between ethyl acetate (50 ml) and water (50 ml)
  3. washThe organic layer was then washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered and pre-adsorbed on to silica
  6. customPurification by silica gel chromatography
  7. washeluting with dichloromethane/methanol/0.88 NH3 (95:4.5:0.5)

Sources & evidence

ORD record
ord-ebe5154da5e140ecbf57c21fbcc3314a
Source dataset
uspto-grants-2004_04
Patent number
US06723735B1

Reaction notes

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