Sodium Carbonate → 5-[4-(Methylsulfonyl)phenyl]-2-nitrothiophene-3-carboxamide

HRID 385714Notes

Reaction equation

HRID 385714 reaction equation
Br[C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([C:10]([NH2:12])=[O:11])[CH:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.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>[CH3:30][S:27]([C:24]1[CH:25]=[CH:26][C:21]([C:2]2[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([C:10]([NH2:12])=[O:11])[CH:3]=2)=[CH:22][CH:23]=1)(=[O:29])=[O:28]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27595302-(4-Methanesulfonylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 534029485-Bromo-2-nitrothiophene-3-carboxamide

Product 1

HCID 595257655-[4-(Methylsulfonyl)phenyl]-2-nitrothiophene-3-carboxamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-2-nitrothiophene-3-carboxamide (1 g, 3.98 mmol), 4,4,5,5-tetramethyl-2-[4-(methylsulfonyl)phenyl]-1,3,2-dioxaborolane (1.236 g, 4.38 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.230 g, 0.199 mmol) were taken up in THF (14 mL)/2 N Na2CO3 (6 mL) The reaction was stirred at 80° C. overnight. Room temperature was attained and the resulting precipitate was collected by filtration, washed with water and triturated in EtOH to give the title compound as a yellow solid.

Workup

  1. customRoom temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customtriturated in EtOH

Sources & evidence

ORD record
ord-4a2d4524a4314dec81cb80128f2914bc
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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