Toluene → HCID 67362201、化合物

HRID 1479932ノート

反応式

HRID 1479932 の反応式
[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]2[CH:21]=[CH:20][C:19](B3OC(C)(C)C(C)(C)O3)=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:31]([O:38][C:39]1[CH:40]=[CH:41][C:42](I)=[C:43]2[C:48]=1[N:47]=[CH:46][CH:45]=[CH:44]2)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].C1(C)C=CC=CC=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>O.CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[Si:31]([O:38][C:39]1[CH:40]=[CH:41][C:42]([C:19]2[CH:18]=[CH:17][C:16]([C:8]3[N:7]([C:11]4[CH:10]=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=4[N:9]=3)=[CH:21][CH:20]=2)=[C:43]2[C:48]=1[N:47]=[CH:46][CH:45]=[CH:44]2)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

参加物

8

反応物 4

HCID 1140TolueneHCID 80271Tri-o-tolylphosphineHCID 596290701-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazoleHCID 68453232HCID 68453232、化合物

生成物 1

HCID 67362201HCID 67362201、化合物

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 1-phenyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-1H-benzimidazole (8.9 g, 22.4 mmol), 8-(tert-butyldimethylsilyl-oxy)-5-iodoquinoline (7.2 g, 18.69 mmol), toluene (110 ml) and dioxane (110 ml) is degassed by passing through of N2 for 30 min. Pd(OAc)2 (9 mg, 0.04 mmol) and tris-o-tolylphosphine (75.6 mg, 0.25 mmol) is then added, and the mixture is heated at 80° C. for 8 h. After cooling to room temperature, the mixture is diluted with water (100 ml) and extracted with ethyl acetate (3×50 ml). The combined organic phases are dried over sodium sulfate, and the solvent is removed under reduced pressure. The crude product is purified by flash chromatography on silica and crystallisation (7.9 g, 80%).

後処理

  1. customis degassed
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customThe crude product is purified by flash chromatography on silica and crystallisation (7.9 g, 80%)

出典と根拠

ORDレコード
ord-f6cc536ea59046cf95c4ac4161e06c7d
出典データセット
uspto-grants-2016_08
特許番号
US09409883B2

反応ノート

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