Water → HCID 86722500, compound

HRID 516486Notes

Reaction equation

HRID 516486 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.Br[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[Br:44].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:44][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=1[C:33]1[C:32]([C:19]2[CH:20]=[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]=2)=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 830602,2'-DibromobiphenylHCID 59629070HCID 59629070, compound

Product 1

HCID 86722500HCID 86722500, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Compound 2 (3.00 g, 7.57 mmol), 2,2′-dibromo-1,1′-biphenyl (4.72 g, 15.1 mmol), tetrakis(triphenylphosphine)palladium(0) (0.350 g, 0.303 mmol), Na2CO3 (3.18 g, 30.0 mmol), H2O (30 mL) and tetrahydrofuran (THF) (50 mL) was degassed with argon for about 44 min while stirring. The reaction mixture was then maintained under argon at about 80° C. while stirring. Upon confirming consumption of the starting material by TLC (SiO2, 19:1-CH2Cl2:acetone), the reaction was cooled to RT and poured over CH2Cl2 (ca. 250 mL). The organics were then washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified via flash chromatography (SiO2, 100% CH2Cl2 to 39:1-CH2Cl2:acetone) to yield Compound 3 (2.34 g, 62%) as an off-white foam: confirmed by LCMS (APCI): calculated for C31H21BrN2 (M+): 501; Found: 501.

Workup

  1. customwas degassed with argon for about 44 min
  2. stirringwhile stirring
  3. customconsumption of the starting material by TLC (SiO2, 19:1-CH2Cl2:acetone)
  4. temperaturethe reaction was cooled to RT
  5. additionpoured over CH2Cl2 (ca. 250 mL)
  6. washThe organics were then washed with H2O and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified via flash chromatography (SiO2, 100% CH2Cl2 to 39:1-CH2Cl2:acetone)

Sources & evidence

ORD record
ord-f735fe31b5b142aca3e1e606f9b3a951
Source dataset
uspto-grants-2015_08
Patent number
US09112159B2

Reaction notes

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