Sodium Carbonate → 3-Benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

HRID 8245Notes

Reaction equation

HRID 8245 reaction equation
Br[C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=2)=[N:5][N:4]2[CH2:14][CH2:15][CH2:16][C:3]=12.[CH2:17]1[O:25][C:24]2[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][C:19]=2[O:18]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CO.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:18]1[C:19]2[CH:20]=[CH:21][C:22]([C:2]3[C:6]([C:7]4[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=4)=[N:5][N:4]4[CH2:14][CH2:15][CH2:16][C:3]=34)=[CH:23][C:24]=2[O:25][CH2:17]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 99002873-bromo-2-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

Product 1

HCID 99230303-Benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromo-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (99 mg, 0.36 mmol), 3,4-methylenedioxyphenylboronic acid (65 mg, 0.39 mmol), (PPh3)4Pd (20 mg, 0.02 mmol), 1 N aqueous sodium carbonate solution (500 μL, 0.5 mmol) in toluene (5 mL) and methanol (1 mL) is purged with argon for 10 min and heated at 80° C. under nitrogen for 30 h. The mixture is cooled and partitioned between water and ethyl acetate, and the organic portion washed with water and brine, dried (sodium sulfate), filtered, and concentrated in vacuo. The crude residue is chromatographed on SiO2 (ethyl acetate) to yield the title compound, 10 mg (9%), as a yellow solid.

Workup

  1. customis purged with argon for 10 min
  2. temperatureThe mixture is cooled
  3. custompartitioned between water and ethyl acetate
  4. washthe organic portion washed with water and brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue is chromatographed on SiO2 (ethyl acetate)

Sources & evidence

ORD record
ord-07ff4df06c1946268840014ad806ef34
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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