Water → 5-(4-Cyanomethyl-phenyl)-thiophene-2-sulfonic acid tert-butylamide

HRID 1696756Notes

Reaction equation

HRID 1696756 reaction equation
[C:1]([NH:5][S:6]([C:9]1[S:10][C:11](Br)=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15]([CH2:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)#[N:16].C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.CCO>[C:1]([NH:5][S:6]([C:9]1[S:10][C:11]([C:21]2[CH:22]=[CH:23][C:18]([CH2:17][C:15]#[N:16])=[CH:19][CH:20]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27571875-Bromo-N-tert-butylthiophene-2-sulfonamideHCID 27733424-(Cyanomethyl)benzeneboronic acid

Product 1

HCID 672735715-(4-Cyanomethyl-phenyl)-thiophene-2-sulfonic acid tert-butylamideYield 40%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-thiophene-2-sulfonic acid tert.-butylamide (0.6 g) was suspended in toluene (5 mL) under an Ar-atmosphere. To the suspension (4-cyanomethylphenyl)boronic acid (486 mg), Na2CO3 (533 mg), water (2.5 ml) and EtOH (2.5 mL) was added. To this suspension 2′-(dimethylamino)-2-biphenyl-palladium (II) chloride dinorbornylphosphine complex (23 mg) was added and the mixture was stirred for 18 h at 80° C. After that the suspension was cooled to 25° C., evaporated to ⅓ of the original volume and treated with EtOAc (30 mL). The organic layer was washed with aqueous HCl (1N, 10 mL) and brine. The organic layer was dried over Na2SO4, filtrated and evaporated to dryness. The crude material was purified by flash chromatography (eluent CH2Cl2, 2N NH3 in methanol) to yield 5-(4-cyanomethyl-phenyl)-thiophene-2-sulfonic acid tert-butylamide (268 mg, 40%) as a light yellow solid.

Workup

  1. additionTo this suspension 2′-(dimethylamino)-2-biphenyl-palladium (II) chloride dinorbornylphosphine complex (23 mg) was added
  2. temperatureAfter that the suspension was cooled to 25° C.
  3. customevaporated
  4. additiontreated with EtOAc (30 mL)
  5. washThe organic layer was washed with aqueous HCl (1N, 10 mL) and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltrated
  8. customevaporated to dryness
  9. customThe crude material was purified by flash chromatography (eluent CH2Cl2, 2N NH3 in methanol)

Sources & evidence

ORD record
ord-a4f1540ef83d45648acb87cbd2ee2916
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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