Tetrahydrofuran → HCID 23025553, compound

HRID 1437477Notes

Reaction equation

HRID 1437477 reaction equation
Br[C:2]1[CH:3]=[C:4]2[NH:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:8][C:5]2=[N:6][CH:7]=1.[C:17]1(OB(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCCC1>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.C(OCC)(=O)C.O1CCCC1>[C:11]1([C:9]2[NH:10][C:4]3[C:5]([N:8]=2)=[N:6][CH:7]=[C:2]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:3]=3)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 47893706-bromo-2-phenyl-1H-imidazo[4,5-b]pyridine

Product 1

HCID 23025553HCID 23025553, compoundYield 22.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
85 °C

Procedure

Under an argon stream, a mixture of 6-bromo-2-phenyl-1H-imidazo[4,5-b]pyridine (Compound of Reference Example 3) (90 mg), phenylboric acid (104 mg), tetrakis(triphenylphosphine)palladium(0) (38 mg), 2 M sodium carbonate (0.82 ml) and tetrahydrofuran (3.3 ml) was stirred at 85° C. for 24 hours. The mixture was distributed into ethyl acetate-tetrahydrofuran (3:1, v/v) and water. The organic layer was washed with water and dried over MgSO4, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-chloroform-hexane (1:1:4, v/v) was concentrated under reduced pressure. The resulting crystals were collected by filtration to obtain 2,6-diphenyl-1H-imidazo[4,5-b]pyridine (20 mg, 22%). The crystals were recrystallized from chloroform-methanol.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. distillationthe solvent was distilled off under reduced pressure
  4. washthe fraction eluted with ethyl acetate-chloroform-hexane (1:1:4, v/v)
  5. concentrationwas concentrated under reduced pressure
  6. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-3fc1db353f07449a8e3c0f8d3a2e7b26
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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