Sodium Carbonate → (E)-3-{1-[4-(1-Methyl-1H-pyrazol-4-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide

HRID 1445493Notes

Reaction equation

HRID 1445493 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)=[O:19])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:28][N:29]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[N:30]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH3:28][N:29]1[CH:33]=[C:32]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([N:11]3[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][O:21][CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][O:23]4)=[O:19])=[CH:12]3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH:31]=[N:30]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86621691(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

Product 1

HCID 86621695(E)-3-{1-[4-(1-Methyl-1H-pyrazol-4-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (966 mg) and 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (662 mg) are dissolved in DME (35 mL) and (Ph3P)3PdCl2 (298 mg) and 2M Na2CO3-solution (3.2 mL) are added. The mixture is heated 16 h to reflux temperature. The mixture is filtered and evaporated and the crude product is purified by silica gel flash chromatography.

Workup

  1. temperatureThe mixture is heated 16 h
  2. temperatureto reflux temperature
  3. filtrationThe mixture is filtered
  4. customevaporated
  5. customthe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-c5fc7167b5984576bea6c6f93b2436b1
Source dataset
uspto-grants-2010_02
Patent number
US07666868B2

Reaction notes

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