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

HRID 1437467
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HRID 1437467 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매
HCID 8028Tetrahydrofuran용매
HCID 21939870Tetrahydrofuran ethyl acetate용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-77b3acd212ef4075a35f01050660df0d
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07622479B2

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