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

HRID 1437467Notes

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

Participants

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

washThe organic layer was washed with water
dry with materialdried over MgSO4
distillationThe solvent was distilled off under reduced pressure
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

Loading…