Sodium Carbonate → HCID 24831572, compound

HRID 2245928Notes

Reaction equation

HRID 2245928 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][N:8]1[CH:12]=[C:11](B2OC(C)(C)C(C)(C)O2)[CH:10]=[N:9]1.BrC1C=C(C2C=NC3N(C(C4(C5C=CC(OC)=CC=5)CC4)=NN=3)N=2)C=CC=1.Br[C:50]1[CH:51]=[C:52]([C:56]2[CH:61]=[N:60][N:59]3[C:62]([C:65]4([C:68]5[CH:73]=[CH:72][C:71]([O:74][CH3:75])=[CH:70][CH:69]=5)[CH2:67][CH2:66]4)=[N:63][N:64]=[C:58]3[N:57]=2)[CH:53]=[CH:54][CH:55]=1>O.C(O)C.C1(C)C=CC=CC=1.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>[CH3:75][O:74][C:71]1[CH:70]=[CH:69][C:68]([C:65]2([C:62]3[N:59]4[N:60]=[CH:61][C:56]([C:52]5[CH:53]=[CH:54][CH:55]=[C:50]([C:11]6[CH:10]=[N:9][N:8]([CH3:7])[CH:12]=6)[CH:51]=5)=[N:57][C:58]4=[N:64][N:63]=3)[CH2:67][CH2:66]2)=[CH:73][CH:72]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 24831408HCID 24831408, compoundHCID 24831409HCID 24831409, compound

Product 1

HCID 24831572HCID 24831572, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

Sodium carbonate (19.1 mg, 0.180 mmol) in water (0.10 mL) was added to a mixture of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (18.7 mg, 0.0900 mmol), tetrakis(triphenylphosphine)palladium(0) (2.0 mg) and a 25.4 mg of a mixture of two regioisomers: 6-(3-bromophenyl)-3-[1-(4-methoxyphenyl)cyclopropyl][1,2,4]triazolo[4,3-b][1,2,4]triazine and 7-(3-bromophenyl)-3-[1-(4-methoxyphenyl)cyclopropyl][1,2,4]-triazolo[4,3-b][1,2,4]triazine in ethanol (300 μL) and toluene (300 μL). The resulting mixture was heated at 150° C. for 1 h. After cooling, the mixture was concentrated and diluted with methanol. The resulting solution was filtered, and the filtrate was subject to preparative RP-HPLC to give the two regioisomers. Analytical LCMS: (M+H)+=424.1. Isomer-I: Rt=1.732 min; Isomer-II: Rt=1.764 min.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. additiondiluted with methanol
  4. filtrationThe resulting solution was filtered
  5. customto give the two regioisomers

Sources & evidence

ORD record
ord-f7fe1c7e61ed4bcdaa5e7bc551960e03
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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