Toluene → HCID 67362201, compound

HRID 1479932Notes

Reaction equation

HRID 1479932 reaction equation
[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]

Participants

8

Reactant 4

HCID 1140TolueneHCID 80271Tri-o-tolylphosphineHCID 59629070HCID 59629070, compoundHCID 68453232HCID 68453232, compound

Product 1

HCID 67362201HCID 67362201, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

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%).

Workup

  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%)

Sources & evidence

ORD record
ord-f6cc536ea59046cf95c4ac4161e06c7d
Source dataset
uspto-grants-2016_08
Patent number
US09409883B2

Reaction notes

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