4-Methylthiophene-2-boronic acid → N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-methyl-4-(4-methyl-2-thienyl)benzenesulfonamide

HRID 130443Notes

Reaction equation

HRID 130443 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]([CH3:28])[CH:3]=1.[CH3:29][C:30]1[CH:31]=[C:32](B(O)O)[S:33][CH:34]=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:32]4[S:33][CH:34]=[C:30]([CH3:29])[CH:31]=4)=[CH:3][C:4]=3[CH3:28])(=[O:10])=[O:9])[CH:17]=2)[CH2:19]1

Participants

7

Reactant 3

HCID 27343734-Methylthiophene-2-boronic acidHCID 23665647Potassium tert-butoxideHCID 590070954-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-methylbenzenesulfonamide

Product 1

HCID 59007047N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-methyl-4-(4-methyl-2-thienyl)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-methylbenzenesulfonamide (E102) (120 mg, 0.26 mmol) and (4-methyl-2-thienyl)boronic acid (73 mg, 0.51 mmol) in DME (3 ml) was added potassium tert-butoxide (263 mg, 2.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (15 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 resulting mixture was then evaporated in vacuo and purified using an SCX cartridge eluting with methanol followed by ammonia (2M in methanol). The appropriate fractions were combined and evaporated in vacuo and the residue purified further by mass directed autoprep HPLC to afford the title compound (E108). MS (ES+) m/e 486 [M+H]+.

Workup

  1. customThe resulting mixture was then evaporated in vacuo
  2. custompurified
  3. washeluting with methanol
  4. customevaporated in vacuo
  5. customthe residue purified further by mass

Sources & evidence

ORD record
ord-391ff44f081c4ac08e13ff4065729423
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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