5-Methyl-2-furanboronic Acid → N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-fluoro-4-(5-methyl-2-furanyl)benzenesulfonamide

HRID 130475Notes

Reaction equation

HRID 130475 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])=[C:4]([F:28])[CH:3]=1.[CH3:29][C:30]1[O:34][C:33](B(O)O)=[CH:32][CH:31]=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:33]4[O:34][C:30]([CH3:29])=[CH:31][CH:32]=4)=[CH:3][C:4]=3[F:28])(=[O:10])=[O:9])[CH:17]=2)[CH2:19]1

Participants

7

Reactant 3

HCID 27343725-Methyl-2-furanboronic AcidHCID 23665647Potassium tert-butoxideHCID 590070834-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-fluorobenzenesulfonamide

Product 1

HCID 24803515N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-fluoro-4-(5-methyl-2-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]-2-fluorobenzenesulfonamide (E103) (200 mg, 0.42 mmol) and (5-methyl-2-furanyl)boronic acid (106 mg, 0.84 mmol) in DME (3 ml) was added potassium tert-butoxide (430 mg, 3.8 mmol) and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 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 in vacuo and residue purified using an SCX column followed by mass directed autoprep HPLC (with addition of 0.1 ml of 10% citric acid in water to the DMSO/MeCN sample to help dissolution) to afford the title compound (E309). MS (ES+) m/e 474 [M+H]+.

Workup

  1. customThe solvent was evaporated in vacuo and residue
  2. custompurified
  3. additionwith addition of 0.1 ml of 10% citric acid in water to the DMSO/MeCN sample
  4. dissolutiondissolution)

Sources & evidence

ORD record
ord-10fdb4f385b845bf99114b2a987c3e4e
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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