Potassium Carbonate → HCID 86712048, compound

HRID 1755517Notes

Reaction equation

HRID 1755517 reaction equation
[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]2[CH:21]=[CH:20][C:19](B3OC(C)(C)C(C)(C)O3)=[CH:18][N:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:32]1[CH:37]=[CH:36][C:35]([Br:38])=[CH:34][N:33]=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>[Br:38][C:35]1[CH:36]=[CH:37][C:32]([C:19]2[CH:18]=[N:17][C:16]([C:8]3[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[N:9]=3)=[CH:21][CH:20]=2)=[N:33][CH:34]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5936905-Bromo-2-iodopyridineHCID 86712047HCID 86712047, compound2×

Product 1

HCID 86712048HCID 86712048, compoundYield 97%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

A mixture of 1-phenyl-2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)-1H-benzo[d]imidazole (Compound 16) (12 mmol), 2-iodo-5-bromo pyridine (6.816 g, 24 mmol), Pd(PPh3)4 (0.69 g, 0.6 mmol) and K2CO3 (3.3 g, 24 mmol) in dioxane/water (100 mL/20 mL) was degassed and heated at 90° C. for 20 hours. The whole was allowed to cool to RT, white precipitate formed. After filtration, a solid (Compound 17) was collected (5.0 g, in 97% yield).

Workup

  1. customwas degassed
  2. temperatureto cool to RT
  3. customwhite precipitate formed
  4. filtrationAfter filtration
  5. customa solid (Compound 17) was collected (5.0 g, in 97% yield)

Sources & evidence

ORD record
ord-abd9cf9e4ba943f781f8c7775ec781dc
Source dataset
uspto-grants-2015_10
Patent number
US09172051B2

Reaction notes

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