Water → HCID 58876089, compound

HRID 2209335Notes

Reaction equation

HRID 2209335 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][CH:19]=[C:18](B3OC(C)(C)C(C)(C)O3)[CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:32]1[C:33]2[C:38]([C:39]([Br:46])=[C:40]3[C:45]=1[CH:44]=[CH:43][CH:42]=[CH:41]3)=[CH:37][CH:36]=[CH:35][CH:34]=2.C([O-])([O-])=O.[Na+].[Na+].O>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.O1CCCC1>[Br:46][C:39]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([C:20]2[CH:21]=[C:16]([C:8]3[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[N:9]=3)[CH:17]=[CH:18][CH:19]=2)=[C:45]2[C:40]=1[CH:41]=[CH:42][CH:43]=[CH:44]2

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 682269,10-DibromoanthraceneHCID 581845421-Phenyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-benzimidazole

Product 1

HCID 58876089HCID 58876089, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

Compound 5 (see WO 2007046658 A1, US 20070205412 A1 and WO 2007086695 A1, which are incorporated by reference herein for their relevant teachings) was prepared as follows: a mixture of Compound 2 (5.270 g, 13.30 mmol), 9,10-dibromoanthracene (13.41 g, 39.90 mmol), tetrakis(triphenylphosphine)palladium(0) (0.922 g, 0.798 mmol), Na2CO3 (9.539 g, 90.00 mmol), H2O (90 mL) and tetrahydrofuran (THF) (150 mL) was degassed with argon for 1.5 h. while stirring. The reaction mixture was then maintained under argon at 85° C. while stirring for 46 h. Upon completion, the reaction was cooled to RT and poured over dichloromethane (about 500 mL). The soluble organics were then washed with H2O and brine, dried over MgSO4, filter and concentrated in vacuo. The crude product was purified via flash chromatography (SiO2, 100% dichloromethane) to provide Compound 5 (5.25 g, 75%) as a light yellow solid.

Workup

  1. customCompound 5 (see WO 2007046658 A1, US 20070205412 A1 and WO 2007086695 A1, which are incorporated by reference herein for their relevant teachings) was prepared
  2. customwas degassed with argon for 1.5 h.
  3. stirringwhile stirring for 46 h
  4. temperatureUpon completion, the reaction was cooled to RT
  5. additionpoured over dichloromethane (about 500 mL)
  6. washThe soluble organics were then washed with H2O and brine
  7. dry with materialdried over MgSO4
  8. filtrationfilter
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified via flash chromatography (SiO2, 100% dichloromethane)

Sources & evidence

ORD record
ord-b36552f85725450d87ad4f932ab16ed8
Source dataset
uspto-grants-2016_06
Patent number
US09379336B2

Reaction notes

Loading…