Potassium Carbonate → 9-(5'-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[3,3'-bipyridin]-5-yl)-9H-carbazole

HRID 520828Notes

Reaction equation

HRID 520828 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[CH:15]=[C:16](B(O)O)[CH:17]=[N:18][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:24]1[CH:25]=[C:26]([C:30]2[N:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:33]3[CH:41]=[CH:42][CH:43]=[CH:44][C:32]=3[N:31]=2)[CH:27]=[N:28][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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>[C:35]1([N:34]2[C:33]3[CH:41]=[CH:42][CH:43]=[CH:44][C:32]=3[N:31]=[C:30]2[C:26]2[CH:25]=[C:24]([C:16]3[CH:17]=[N:18][CH:19]=[C:14]([N:12]4[C:13]5[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=5[C:6]5[C:11]4=[CH:10][CH:9]=[CH:8][CH:7]=5)[CH:15]=3)[CH:29]=[N:28][CH:27]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 230940852-(5-bromopyridine-3-yl)-1-phenyl-1H-benzimidazoleHCID 86679311(5-(9H-carbazol-9-yl)pyridin-3-yl)boronic acid

Product 1

HCID 894553649-(5'-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[3,3'-bipyridin]-5-yl)-9H-carbazoleYield 49%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of (5-(9H-carbazol-9-yl)pyridin-3-yl)boronic acid (2C) (0.90 g, 3.1 mmol), 2-(5-bromopyridin-3-yl)-1-phenyl-1H-benzo[d]imidazole (1F) (0.856 g, 3.1 mmol), Pd(PPh3)4 (0.18 g, 0.155 mmol) and potassium carbonate (1.07 g, 7.8 mmol) in dioxane/water (20 mL/5 mL) was degassed and heated at about 90° C. overnight under argon atmosphere. The whole was poured into ethyl acetate (100 mL), then washed with brine (50 mL). The organic phase was collected and dried over Na2SO4, absorbed on silica gel, then purified by flash column (dichloromethane/methanol 40:1) to give a light yellow solid (0.78 g), which was purified again by flash column (silica gel, dichloromethane/methanol 50:1) followed by recrystallization in dichloromethane/methanol to give HTH-2, a light yellow solid (0.60 g, 38% yield).

Workup

  1. customwas degassed
  2. additionThe whole was poured into ethyl acetate (100 mL)
  3. washwashed with brine (50 mL)
  4. customThe organic phase was collected
  5. dry with materialdried over Na2SO4
  6. customabsorbed on silica gel
  7. custompurified by flash column (dichloromethane/methanol 40:1)

Sources & evidence

ORD record
ord-238e8226a388425b8855360fc0db1fb6
Source dataset
uspto-grants-2016_05
Patent number
US09328094B2

Reaction notes

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