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Toluene → 2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridine

HRID 1437467
Notes
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Reaction equation

HRID 1437467 reaction equation
Br[C:2]1[CH:3]=[C:4]2[NH:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)=[N:8][C:5]2=[N:6][CH:7]=1.[C:19]1(OB(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>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.O1CCCC1>[CH3:18][O:17][C:13]1[CH:12]=[C:11]([C:9]2[NH:10][C:4]3[C:5]([N:8]=2)=[N:6][CH:7]=[C:2]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:3]=3)[CH:16]=[CH:15][CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 230258076-bromo-2-(3-methoxyphenyl)-1H-imidazo[4,5-b]pyridine

Product 1

HCID 99483042-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridineYield 66.3%

Reagents, catalysts & solvents 4

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent
HCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
90 °C

Procedure

Under an argon stream, a mixture of 6-bromo-2-(3-methoxyphenyl)-1H-imidazo[4,5-b]pyridine (Compound of Reference Example 2) (21.3 g), phenylboric acid (22.2 g), tetrakis(triphenylphosphine)palladium(0) (7.60 g), 2 M sodium carbonate (175 ml), toluene (525 ml) and tetrahydrofuran (175 ml) was stirred at 90° C. for 24 hours. The reaction mixture was distributed into ethyl acetate-tetrahydrofuran (3:1, v/v) and water. The organic layer was washed with water, dried over MgSO4. The solvent was distilled off under reduced pressure, and the resulting crystals were collected by filtration to obtain 2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridine (14.0 g, 66%). 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. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-77b3acd212ef4075a35f01050660df0d
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07622479B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes