Potassium Phosphate, Tribasic → HCID 22727960, compound

HRID 2086085Notes

Reaction equation

HRID 2086085 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][N:8]([C:11]3[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=3)[C:5]2=[N:6][CH:7]=1.[O:18]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.[OH-].[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:18]1[CH:22]=[CH:21][C:20]([C:2]2[CH:3]=[C:4]3[N:10]=[CH:9][N:8]([C:11]4[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=4)[C:5]3=[N:6][CH:7]=2)=[CH:19]1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734358Furan-3-boronic acidHCID 22727953HCID 22727953, compound

Product 1

HCID 22727960HCID 22727960, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(6-bromoimidazo[4,5-b]pyridin-3-yl)phenol (2.32 g, 8 mmol), 3-furanboronic acid (1.43 g, 12.8 mmol), potassium phosphate (3.4 g, 16 mmol) and tetrakis(triphenylphosphine)palladium(0) (370 mg) in degassed N,N-dimethylformamide (12 ml) was heated at 80° C. for 20 hours. After cooling to ambient temperature the mixture was dissolved in 3N sodium hydroxide and extracted with dichloromethane, then with ether. The aqueous phase was adjusted to pH 7 with concentrated hydrochloric acid and the resulting solid collected by filtration, washed with water and dried under high vacuum to afford 3-[6-(furan-3-yl)imidazo[4,5-b]pyridin-3-yl]phenol as a cream-coloured solid (2.2 g, 99%); δH (400 MHz, d6-DMSO) 6.86 (1H, ddd, J 8, 2 and 1), 7.15 (1H, s), 7.33-7.45 (3H, m), 7.81 (1H, s), 8.35 (1H, s), 8.46 (1H, d, J 2), 8.54 (1H, d, J 2), 8.91 (1H, s), 9.94 (1H, br s); m/z (ES+) 278 (M++H).

Workup

  1. temperatureAfter cooling to ambient temperature the mixture
  2. extractionextracted with dichloromethane
  3. filtrationthe resulting solid collected by filtration
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-c94f88a64eae4d71b9271593055af012
Source dataset
uspto-grants-2004_04
Patent number
US06723735B1

Reaction notes

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