Sodium Carbonate → 1,1-Dimethylethyl 4-(6-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1,2-benzisoxazol-3-yl)-1-piperazinecarboxylate

HRID 1988886Notes

Reaction equation

HRID 1988886 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]2[C:6]([N:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[CH:24]1([NH:27][C:28](=[O:45])[C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[C:31](B3OC(C)(C)C(C)(C)O3)[CH:30]=2)[CH2:26][CH2:25]1.C(=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:24]1([NH:27][C:28]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[C:31]([C:2]3[CH:23]=[CH:22][C:5]4[C:6]([N:9]5[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]5)=[N:7][O:8][C:4]=4[CH:3]=3)[CH:30]=2)=[O:45])[CH2:25][CH2:26]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide2×HCID 586564881,1-Dimethylethyl 4-(6-bromo-1,2-benzisoxazol-3-yl)-1-piperazinecarboxylate2×

Product 1

HCID 586564681,1-Dimethylethyl 4-(6-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1,2-benzisoxazol-3-yl)-1-piperazinecarboxylateYield 60.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 1,1-dimethylethyl 4-(6-bromo-1,2-benzisoxazol-3-yl)-1-piperazinecarboxylate (Intermediate 25) (0.04 g), N-Cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 5) (0.035 g), 2N aqueous sodium carbonate (2 ml) and tetrakis(triphenylphosphine)palladium(0) (1 mg) in isopropanol (6 ml) was stirred at reflux under nitrogen for 16 h. The residue was absorbed onto silica Merck 7734) and applied to a Varian Bond-Elut SPE cartridge (silica, 5 g). Elution with dichloromethane:methanol (98:2) gave the title compound as a cream solid (0.03 g).

Workup

  1. temperatureat reflux under nitrogen for 16 h
  2. customThe residue was absorbed onto silica Merck 7734) and
  3. washElution with dichloromethane:methanol (98:2)

Sources & evidence

ORD record
ord-06d94b80965d4de795742d81c49dda4e
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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