Potassium Carbonate → HCID 6620889, compound

HRID 579684Notes

Reaction equation

HRID 579684 reaction equation
C(C1C2NC3C(=CC=CC=3)C=2C=CC=1)C(C)C.CC1(C)C(C)(C)OB(C2C=CC(CCC[C:35]3[CH:36]=[CH:37][C:38]4[N:39]([CH2:66][CH:67]([CH3:69])[CH3:68])[C:40]5[C:45]([C:46]=4[CH:47]=3)=[CH:44][C:43](CCCC3C=CC(B4OC(C)(C)C(C)(C)O4)=CC=3)=[CH:42][CH:41]=5)=CC=2)O1.BrC1C=CC=C(Br)N=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.O.C1COCC1>[CH3:68][CH:67]([CH3:69])[CH2:66][N:39]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:45]=2[C:46]2[C:38]1=[CH:37][CH:36]=[CH:35][CH:47]=2

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 122742,6-DibromopyridineHCID 67539664HCID 67539664, compoundHCID 86643573HCID 86643573, compound

Product 1

HCID 6620889HCID 6620889, compoundYield 175.3%

Reagents, catalysts & solvents 4

HCID 80271Tri-o-tolylphosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

Polymer 1—poly(iso-butylcarbazole-co-biphenylpyridine). Into a mixture of 36 (0.200 g, 0.281 mmol), 2,6-dibromopyridine (0.067 g, 0.281 mmol), Pd2(dba)3 (6.4 mg, 7.0 μmol), tri(o-tolyl)phosphine (8.6 mg, 28 μmol) and K2CO3 (0.387 g, 2.81 mmol) was added THF (4.2 mL) and H2O (1.4 mL). The reaction mixture was stirred at 85° C. under dark for 48 hours before cooling to room temperature. The aqueous solution was removed with a pipette. The organic phase was diluted with chloroform, and washed with 5% aqueous NaCN solution till no further bleaching occurs. The organic solution was concentrated and precipitated in methanol and then in hexane. The collected solid was subjected to Soxhlet extraction with methanol, hexane and acetone to yield Polymer 1 as a white solid (0.11 g, 69%). 1H NMR (400 MHz, CDCl3, 298 K): δ(ppm) 8.05-8.03 (d, J=8 Hz, 4H), 7.88 (s, 1H), 7.71-7.66 (m, 1H), 7.58-7.57 (m, 2H), 7.36-7.20 (m, 7H), 4.01-3.99 (d, 2H), 2.85-2.81 (t, 4H), 2.76-2.72 (t, 4H), 2.35-2.28 (m, 1H), 2.11-2.02 (m, 4H), 0.95-0.93 (d, 6H). MW=80,100, Mn=21,900.

Workup

  1. temperaturebefore cooling to room temperature
  2. customThe aqueous solution was removed with a pipette
  3. additionThe organic phase was diluted with chloroform
  4. washwashed with 5% aqueous NaCN solution till no further bleaching
  5. concentrationThe organic solution was concentrated
  6. customprecipitated in methanol
  7. extractionThe collected solid was subjected to Soxhlet extraction with methanol, hexane and acetone

Sources & evidence

ORD record
ord-492e55b00f644bdea83b72281c2e6da8
Source dataset
uspto-grants-2015_05
Patent number
US09040718B2

Reaction notes

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