Potassium Carbonate → HCID 86712046, compound

HRID 1755515Notes

Reaction equation

HRID 1755515 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.[Br:31][C:32]1[CH:37]=[CH:36][C:35](I)=[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:31][C:32]1[N:33]=[CH:34][C:35]([C:19]2[CH:18]=[N:17][C:16]([C:8]3[N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[N:9]=3)=[CH:21][CH:20]=2)=[CH:36][CH:37]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 47382712-Bromo-5-iodopyridineHCID 86712047HCID 86712047, compound2×

Product 1

HCID 86712046HCID 86712046, compoundYield 61%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °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 (3 mmol), 2-bromo-5-iodopyridine (1.98 g, 7 mmol) (Compound 10), Pd(PPh3)4 (0.346 g, 0.3 mmol) and potassium carbonate (0.828 g, 6 mmol) in dioxane/water (50 mL/10 mL) was degassed and heated at about 80° C. overnight. The mixture was poured into ethyl acetate (250 mL), washed with water, then brine, dried over Na2SO4, loaded on silica gel and purified by flash column (hexanes/dichloromethane 1:1 to dichloromethane to dichloromethane/ethyl acetate 9:1 to 4:1). The desired fraction was collected and concentrated, then filtered to give a light yellow solid (Compound 11) (0.78 g, in 61% yield).

Workup

  1. customwas degassed
  2. additionThe mixture was poured into ethyl acetate (250 mL)
  3. washwashed with water
  4. dry with materialbrine, dried over Na2SO4
  5. custompurified by flash column (hexanes/dichloromethane 1:1 to dichloromethane to dichloromethane/ethyl acetate 9:1 to 4:1)
  6. customThe desired fraction was collected
  7. concentrationconcentrated
  8. filtrationfiltered

Sources & evidence

ORD record
ord-6d7a274a66e94c3aaedfb3f61820c8ea
Source dataset
uspto-grants-2015_10
Patent number
US09172051B2

Reaction notes

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