Sodium Carbonate → N-Cyclopropyl-4-methyl-3-{3-[(4-methyl-1-piperazinyl)methyl]-1,2-benzisoxazol-6-yl}benzamide

HRID 1988927Notes

Reaction equation

HRID 1988927 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]2[C:6]([CH2:9][N:10]3[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)=[N:7][O:8][C:4]=2[CH:3]=1.[CH:19]1([CH2:22][NH:23][C:24](=[O:40])[C:25]2[CH:30]=[CH:29][CH:28]=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:26]=2)[CH2:21]C1.[C:41](=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C.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>[CH:22]1([NH:23][C:24](=[O:40])[C:25]2[CH:26]=[CH:27][C:28]([CH3:41])=[C:29]([C:2]3[CH:18]=[CH:17][C:5]4[C:6]([CH2:9][N:10]5[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]5)=[N:7][O:8][C:4]=4[CH:3]=3)[CH:30]=2)[CH2:19][CH2:21]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 586565076-Bromo-3-[(4-methyl-1-piperazinyl)methyl]-1,2-benzisoxazole2×HCID 68676775HCID 68676775, compound2×

Product 1

HCID 10408949N-Cyclopropyl-4-methyl-3-{3-[(4-methyl-1-piperazinyl)methyl]-1,2-benzisoxazol-6-yl}benzamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 6-bromo-3-[(4-methyl-1-piperazinyl)methyl]-1,2-benzisoxazole (Intermediate 46) (0.02 g) N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 5) (0.02 g) 2N aqueous sodium carbonate and tetrakis(triphenylphosphine)palladium(0) (1 mg) in isopropanol (0.3 ml) was heated in a Reactivial™ at 65° for 18 h. the reaction mixture was partitioned between water and ethyl acetate, the phases were separated and the aqueous layer was re-extracted with ethyl acetate. The combined organic extracts were washed with water (×2) and brine, dried using a hydrophobic filter tube and concentrated under a stream of nitrogen. The residue was purified by reverse phase preparative Hplc to give the title compound as a white foam (0.006 g).

Workup

  1. temperaturewas heated in a Reactivial™ at 65° for 18 h. the reaction mixture
  2. customwas partitioned between water and ethyl acetate
  3. customthe phases were separated
  4. extractionthe aqueous layer was re-extracted with ethyl acetate
  5. washThe combined organic extracts were washed with water (×2) and brine
  6. customdried
  7. concentrationconcentrated under a stream of nitrogen
  8. customThe residue was purified by reverse phase preparative Hplc

Sources & evidence

ORD record
ord-0d1e0d5e71884d229dab49ae44c5d0c1
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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