Sodium Carbonate → HCID 89456211, compound

HRID 1050698Notes

Reaction equation

HRID 1050698 reaction equation
Br[C:2]1[C:10]2[C:6](=[N:7][N:8]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)[N:9]=2)[C:5]([Br:17])=[CH:4][CH:3]=1.[CH2:18]([C:24]1([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:36]2[CH:35]=[C:34](B(O)O)[CH:33]=[CH:32][C:31]=2[C:30]2[C:25]1=[CH:26][C:27](B(O)O)=[CH:28][CH:29]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[Na+].[Na+].[Br:55][C:56]1[CH:61]=[CH:60][C:59](CCCC)=[CH:58][CH:57]=1>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.C1(C)C=CC=CC=1.C(O)CCC>[Br:17][C:5]1[C:6]2=[N:7][N:8]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)[N:9]=[C:10]2[C:2]([C:27]2[CH:28]=[CH:29][C:30]3[C:31]4[C:36](=[CH:35][C:34]([C:59]5[C:58]6[C:57](=[N:7][N:8]([C:11]7[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=7)[N:9]=6)[C:56]([Br:55])=[CH:61][CH:60]=5)=[CH:33][CH:32]=4)[C:24]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:25]=3[CH:26]=2)=[CH:3][CH:4]=1

Participants

9

Reactant 4

HCID 10340Sodium Carbonate2×HCID 5210591-Bromo-4-butylbenzeneHCID 45242859,9-Dihexylfluorene-2,7-diboronic acidHCID 866799014,7-dibromo-2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole

Product 1

HCID 89456211HCID 89456211, compoundYield 10.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 2631-ButanolSolventHCID 962WaterSolvent3×HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of Intermediate A (3.52 g, 10 mmol), 9,9-dihexylfluorene-2,7-diboronic acid (1.90 g, 4.5 mmol), sodium carbonate (2.12 g, 20 mmol) in water (10 mL), tetrakis(triphenylphosphine)palladium (0) (1.00 g, 0.86 mmol), n-butanol (80 mL), and toluene (20 mL) was stirred and heated under argon at 110° C. After 48 hours, 1-bromo-4-butylbenzene (3.0 mL, 17 mmol) was added followed by sodium carbonate (2.12 g, 20 mmol) in water (10 mL) and tetrakis(triphenylphosphine)palladium (0) (1.00 g, 0.86 mmol), and heating was continued for an additional 20 hours. The reaction mixture was poured into water (200 mL and extracted with ethyl acetate). The extract was dried over anhydrous sodium sulfate, the volatiles were removed under reduced pressure, and the residue was chromatographed (silica gel, dichloromethane/ethyl acetate 3:1). The first fraction gave Intermediate E (414 mg, 10%).

Workup

  1. temperatureheating
  2. waitwas continued for an additional 20 hours
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe volatiles were removed under reduced pressure
  5. customthe residue was chromatographed (silica gel, dichloromethane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-5a292f47e5314c2781abc66bdf041f00
Source dataset
uspto-grants-2016_07
Patent number
US09382424B2

Reaction notes

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