Furan-3-boronic acid → N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-3-fluoro-4-(3-furanyl)benzenesulfonamide

HRID 130450Notes

Reaction equation

HRID 130450 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([N:18]3[CH2:23][C@H:22]([CH3:24])[NH:21][C@H:20]([CH3:25])[CH2:19]3)[CH:15]=[CH:14][C:13]=2[O:26][CH3:27])(=[O:10])=[O:9])=[CH:4][C:3]=1[F:28].[O:29]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30]1.CC(C)([O-])C.[K+]>COCCOC.O.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>[CH3:25][C@H:20]1[NH:21][C@@H:22]([CH3:24])[CH2:23][N:18]([C:16]2[CH:15]=[CH:14][C:13]([O:26][CH3:27])=[C:12]([NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([C:31]4[CH:32]=[CH:33][O:29][CH:30]=4)=[C:3]([F:28])[CH:4]=3)(=[O:10])=[O:9])[CH:17]=2)[CH2:19]1

Participants

7

Reactant 3

HCID 2734358Furan-3-boronic acidHCID 23665647Potassium tert-butoxideHCID 590070604-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-3-fluorobenzenesulfonamide

Product 1

HCID 11604977N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-3-fluoro-4-(3-furanyl)benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-3-fluorobenzenesulfonamide (E105) (100 mg, 0.21 mmol) and 3-furanylboronic acid (47 mg, 0.42 mmol) in DME (3 ml) was added potassium tert-butoxide (212 mg, 1.89 mmol) and tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.01 mmol) in water (1 ml) and the resulting mixture stirred in a microwave (set at high absorbance) at 100° C. for 30 minutes. The solvent was evaporated with the addition of a few drops of toluene and the residue passed through an SCX column eluting with methanol followed by 2M ammonia in methanol. The basic fractions were combined and the solvent evaporated. The crude product was purified by mass directed autoprep HPLC and the relevant fractions collected and solvent evaporated to afford the title compound (E116). MS (ES+) m/e 460 [M+H]+.

Workup

  1. customThe solvent was evaporated with the addition of a few drops of toluene
  2. washeluting with methanol
  3. customthe solvent evaporated
  4. customThe crude product was purified by mass
  5. customthe relevant fractions collected
  6. customsolvent evaporated

Sources & evidence

ORD record
ord-a361d1dc1ed04f979c7b73e8f1860c76
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

Loading…