Toluene → HCID 67541261, compound

HRID 579677Notes

Reaction equation

HRID 579677 reaction equation
C1(C)C=CC=CC=1.[CH3:8][CH:9]([CH3:33])[CH2:10][N:11]1[C:23]2[CH:22]=[CH:21][C:20](B3OC(C)(C)C(C)(C)O3)=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2.Br[C:35]1[CH:36]=[CH:37][C:38]2[N:39]([CH2:49][CH:50]([CH3:52])[CH3:51])[C:40]3[C:45]([C:46]=2[CH:47]=1)=[CH:44][C:43]([Br:48])=[CH:42][CH:41]=3.C([O-])([O-])=O.[Na+].[Na+]>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.O>[Br:48][C:43]1[CH:44]=[CH:45][C:40]2[N:39]([CH2:49][CH:50]([CH3:51])[CH3:52])[C:38]3[C:37]([C:41]=2[CH:42]=1)=[CH:36][C:35]([C:15]1[CH:14]=[CH:13][C:12]2[N:11]([CH2:10][CH:9]([CH3:33])[CH3:8])[C:23]4[C:18]([C:17]=2[CH:16]=1)=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:47][CH:46]=3

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 57668735HCID 57668735, compoundHCID 67539983HCID 67539983, compound

Product 1

HCID 67541261HCID 67541261, compoundYield 34.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Toluene (30 ml) and H2O (10 ml) were added into a mixture of 4 (1.2 g, 3.43 mmol), 2 (3.27 g, 8.59 mmol), Pd(PPh3)4 (0.22 g, 0.17 mmol) and Na2CO3 (3.43 g, 34 mmol). The reaction mixture was stirred at 90° C. for 12 hours, cooled to room temperature, and then extracted with methylene chloride. The organic extracts were combined, washed with water, and dried over MgSO4. Upon evaporating off the solvent, the crude product was purified by gradient column chromatography on silica gel with hexane/methylene chloride 9:1 to 3:1 (v/v) to yield 5 (0.62 g, 34%) as a white powder. 1H NMR (400 MHz, CDCl3, 298 K): δ(ppm) 8.40-8.33 (dd, 2H), 8.30-8.28 (d, 1H), 8.21-8.35 (d, 1H), 7.88-7.76 (m, 2H), 7.56-7.40 (m, 5H), 7.33-7.20 (m, 2H), 4.14-4.09 (m, 4H), 2.46-2.37 (m, 2H), 1.10-0.90 (m, 12H).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with methylene chloride
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customUpon evaporating off the solvent
  6. customthe crude product was purified by gradient column chromatography on silica gel with hexane/methylene chloride 9:1 to 3:1 (v/v)

Sources & evidence

ORD record
ord-7812919247bc42978110a37e9856e2fe
Source dataset
uspto-grants-2015_05
Patent number
US09040718B2

Reaction notes

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