Sodium Carbonate → 9-(3-(5-(1-phenyl-1H-benzo[d]imidazol-2-yl)pyridin-3-yl)phenyl)-9H-carbazole

HRID 520825Notes

Reaction equation

HRID 520825 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([N:15]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:21]4[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:12]=[CH:13][CH:14]=2)O1.Br[C:30]1[CH:31]=[C:32]([C:36]2[N:40]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:39]3[CH:47]=[CH:48][CH:49]=[CH:50][C:38]=3[N:37]=2)[CH:33]=[N:34][CH:35]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[C:41]1([N:40]2[C:39]3[CH:47]=[CH:48][CH:49]=[CH:50][C:38]=3[N:37]=[C:36]2[C:32]2[CH:31]=[C:30]([C:13]3[CH:12]=[C:11]([N:15]4[C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=5[C:22]5[C:27]4=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH:10]=[CH:9][CH:14]=3)[CH:35]=[N:34][CH:33]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 230940852-(5-bromopyridine-3-yl)-1-phenyl-1H-benzimidazoleHCID 58690899(3-(carbazole-9H)Phenyl)Pinacol ester

Product 1

HCID 866793109-(3-(5-(1-phenyl-1H-benzo[d]imidazol-2-yl)pyridin-3-yl)phenyl)-9H-carbazoleYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 1C (3.0 g, 8.15 mmol), compound 1F (2.85 g, 8.15 mmol), tetrakistriphenylphosphine palladium (471 mg, 0.408 mmol), and sodium carbonate (3.09 g, 29.2 mmol) in tetrahydrofuran (THF)/water (50 mL/30 mL) was degassed for about 45 minutes. The mixture then heated to reflux (about 80° C.) overnight under argon. After cooling to RT, the reaction mixture was poured into DCM (300 mL) then washed with saturated sodium bicarbonate (200 mL), water (200 mL), and brine (200 mL). The organic phase was then collected, dried over magnesium sulfate, and loaded onto silica gel. A flash column (gradient of 25% to 40% ethyl acetate in DCM) and precipitation from ethyl acetate/methanol gave 2.34 g of HTH-1; 56% yield, pure by HNMR.

Workup

  1. customwas degassed for about 45 minutes
  2. temperatureThe mixture then heated
  3. temperatureAfter cooling to RT
  4. additionthe reaction mixture was poured into DCM (300 mL)
  5. washthen washed with saturated sodium bicarbonate (200 mL), water (200 mL), and brine (200 mL)
  6. customThe organic phase was then collected
  7. dry with materialdried over magnesium sulfate
  8. customA flash column (gradient of 25% to 40% ethyl acetate in DCM) and precipitation from ethyl acetate/methanol
  9. customgave 2.34 g of HTH-1

Sources & evidence

ORD record
ord-5ac94c479fd543a099b62b2a86a06e32
Source dataset
uspto-grants-2016_05
Patent number
US09328094B2

Reaction notes

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