Sodium Carbonate → HCID 86686621, compound

HRID 84771Notes

Reaction equation

HRID 84771 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([C:13](=[O:23])[CH2:14][N:15]2[C:19]([Br:20])=[C:18]([Br:21])[N:17]=[C:16]2Br)[CH2:9][CH2:8]1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>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.O.O1CCOCC1>[Br:21][C:18]1[N:17]=[C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:15]([CH2:14][C:13]([N:10]2[CH2:11][CH2:12][N:7]([C:2]3[N:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:8][CH2:9]2)=[O:23])[C:19]=1[Br:20]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 866866201-(4-Pyrimidin-2-yl-piperazin-1-yl)-2-(2,4,5-tribromo-imidazol-1-yl)-ethanone

Product 1

HCID 86686621HCID 86686621, compoundYield 79.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

1.7 g tetrakis was added to a stirred mixture of 15 g 1-(4-pyrimidin-2-yl-piperazin-1-yl)-2-(2, 4, 5-tribromo-imidazol-1-yl)-ethanone, 3.6 g phenylboronic acid, 9.4 g sodiumcarbonate, 250 mL dioxane and 50 mL water under nitrogen atmosphere. The reaction mixture was stirred 3 h at 85° C. Sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated. Diisopropylether was added to the residue and the precipitate was filtered to give 11.8 g desired product. Rt: 0.87 (method B), ESI+: 505

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. additionDiisopropylether was added to the residue
  6. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-6a83590b5777414ba28d851ecfeaac38
Source dataset
uspto-grants-2014_09
Patent number
US08846948B2

Reaction notes

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