Toluene → HCID 67362201, 화합물

HRID 1479932노트

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HRID 1479932 반응식
[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]

참가 물질

8

반응물 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, 화합물

생성물 1

HCID 67362201HCID 67362201, 화합물

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-f6cc536ea59046cf95c4ac4161e06c7d
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409883B2

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