Ethanol → tert-butyl N-[4-[[5-(2-methylphenyl)-3-pyridinyl]sulfonyl]-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 723087Notes

Reaction equation

HRID 723087 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]([C:10]1[S:11][C:12]([S:25][CH3:26])=[C:13]([S:15]([C:18]2[CH:19]=[N:20][CH:21]=[C:22](Br)[CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[CH3:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C(O)C>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.CCOC(C)=O.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8](=[NH:9])[C:10]1[S:11][C:12]([S:25][CH3:26])=[C:13]([S:15]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[CH3:28])[CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 145857652tert-butyl N-[4-[(5-bromo-3-pyridinyl)sulfonyl]-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857698tert-butyl N-[4-[[5-(2-methylphenyl)-3-pyridinyl]sulfonyl]-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The procedure described in Example 1: step c was followed using {[4-(5-Bromo-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (50 mg, 0.08 mmol), 2-methyl phenyl boronic acid (23 mg, 0.17 mmol), Pd(PPh3)4 (19 mg, 0.02 mmol), aqueous Na2CO3 (2M, 800 μL, 0.4 mmol), ethanol (800 μL) and toluene (1600 μL). The reaction was heated to 80° C. for 12 hours. The residue was dissolved into EtOAc and washed with brine. The organic layers were dried (MgSO4) and removal of the solvents in vacuo resulted in a crude mixture of the product that was used without further purification or characterization.

Workup

  1. washwashed with brine
  2. customThe organic layers were dried
  3. custom(MgSO4) and removal of the solvents in vacuo
  4. customresulted in a crude
  5. additionmixture of the product that
  6. customwas used without further purification or characterization

Sources & evidence

ORD record
ord-62a02fd98ed644c0aa565b11269fe338
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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