Sodium Carbonate → 3-{3-[2-(2-Ethylimidazol-1-yl)acetyl]phenyl}-5-iso-butyl-N-tert-butylthio-phene-2-sulfonamide

HRID 659699Notes

Reaction equation

HRID 659699 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8](=[O:17])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1.[CH2:18]([C:22]1[S:26][C:25]([S:27]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])=[O:28])=[C:24](B(O)O)[CH:23]=1)[CH:19]([CH3:21])[CH3:20].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.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>[CH2:15]([C:11]1[N:10]([CH2:9][C:8]([C:4]2[CH:3]=[C:2]([C:24]3[CH:23]=[C:22]([CH2:18][CH:19]([CH3:20])[CH3:21])[S:26][C:25]=3[S:27]([NH:30][C:31]([CH3:33])([CH3:32])[CH3:34])(=[O:29])=[O:28])[CH:7]=[CH:6][CH:5]=2)=[O:17])[CH:14]=[CH:13][N:12]=1)[CH3:16]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 11484000(2-(N-(tert-Butyl)sulfamoyl)-5-isobutylthiophen-3-yl)boronic acidHCID 614053531-(3-Bromophenyl)-2-(2-ethylimidazol-1-yl)ethanone

Product 1

HCID 671329483-{3-[2-(2-Ethylimidazol-1-yl)acetyl]phenyl}-5-iso-butyl-N-tert-butylthio-phene-2-sulfonamideYield 94%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(3-bromophenyl)-2-(2-ethylimidazol-1-yl)ethanone (54.6 mg, 0.186 mmol; see step (a)) in toluene (10 mL) and ethanol (1 mL) was added 5-isobutyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (101 mg, 0.317 mmol; see Example 1(c)), Pd(PPh3)4 (12.9 mg, 0.0112 mmol), Na2CO3 (373 μL, 0.745 mmol, 2.0 M aq) and the reaction mixture was stirred for 4 h at 80° C. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc. The combined organic phase was dried (over anhydrous MgSO4), concentrated in vacuo, and the residue purified by flash chromatography using MeOH:CH2Cl2 (5:95) as eluent to give the sub-title compound as a colourless syrup in 94% yield (85.5 mg, 0.175 mmol).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phase was dried (over anhydrous MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-beec73cb9e194f069c0d3154decc27c4
Source dataset
uspto-grants-2011_12
Patent number
US08080571B2

Reaction notes

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