4-Methylthiophene-2-boronic acid → HCID 59007074, compound

HRID 130448Notes

Reaction equation

HRID 130448 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]([Cl: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>[Cl:28][C:4]1[CH:3]=[C:2]([C:32]2[S:33][CH:34]=[C:30]([CH3:29])[CH:31]=2)[CH:7]=[CH:6][C:5]=1[S:8]([NH:11][C:12]1[CH:17]=[C:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[NH:21][C@H:20]([CH3:25])[CH2:19]2)[CH:15]=[CH:14][C:13]=1[O:26][CH3:27])(=[O:10])=[O:9]

Participants

7

Reactant 3

HCID 27343734-Methylthiophene-2-boronic acid2×HCID 23665647Potassium tert-butoxideHCID 590070594-Bromo-2-chloro-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]benzenesulfonamide

Product 1

HCID 59007074HCID 59007074, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-bromo-2-chloro-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]benzenesulfonamide (E104) (70 mg, 0.14 mmol) and (4-methyl-2-thienyl)boronic acid (40 mg, 0.28 mmol) in DME (3 ml) was added potassium tert-butoxide (142 mg, 1.26 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. Additional (4-methyl-2-thienyl)boronic acid (20 mg, 0.14 mmol) and tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.01 mmol) were then added and the mixture stirred in a microwave (set at high absorbance) at 100° C. for a further 30 minutes. The solvent was evaporated after transfer to a new flask with methanol and a few drops of toluene and the residue passed through an SCX column eluting with methanol followed by 2M ammonia in methanol. The appropriate fractions were collected and evaporated in vacuo and the residue purified further by mass directed autoprep HPLC to afford the title compound (E113). MS (ES+) m/e 506/508 [M+H]+.

Workup

  1. stirringthe mixture stirred in a microwave (set at high absorbance) at 100° C. for a further 30 minutes
  2. customThe solvent was evaporated after transfer to a new flask with methanol and a few drops of toluene
  3. washeluting with methanol
  4. customThe appropriate fractions were collected
  5. customevaporated in vacuo
  6. customthe residue purified further by mass

Sources & evidence

ORD record
ord-9c997f95c6094ceb9225f93833c4356e
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

Loading…