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

HRID 1437467
ノート
印刷プレビュー

反応式

HRID 1437467 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 21939870Tetrahydrofuran ethyl acetate溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-77b3acd212ef4075a35f01050660df0d
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07622479B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート