2-Thiopheneboronic acid → HCID 86756255, compound

HRID 567076Notes

Reaction equation

HRID 567076 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:13])([CH3:12])[CH2:6][CH:5]2[CH2:14][NH:15][S:16]([CH2:19][CH3:20])(=[O:18])=[O:17].[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1B(O)O>C1(C)C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:12][C:7]1([CH3:13])[CH2:6][CH:5]([CH2:14][NH:15][S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:22]3[S:21][CH:25]=[CH:24][CH:23]=3)[CH:3]=2)[O:8]1

Participants

7

Reactant 2

HCID 27339602-Thiopheneboronic acidHCID 86756256HCID 86756256, compound

Product 1

HCID 86756255HCID 86756255, compoundYield 71.1%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 10796Cesium carbonateSolvent

Conditions

Temperature
80 °C

Procedure

410 mg (1 mmol) of ethanesulfonic acid (6-iodo-2,2-dimethylchroman-4-yl)methylamide were dissolved in 5 ml of toluene and 130 mg (1 mmol) of thiopheneboronic acid, 40 mg of palladium tetrakis(triphenylphosphine) in 5 ml of ethanol and 1.1 ml of 2-molar cesium carbonate solution were added. The mixture was stirred overnight at 80° C. After removing the solvent, the residue was taken up in methylene chloride and washed with water. After drying and removing the solvent, the residue obtained was purified by column chromatography (eluent heptane/ethyl acetate 1:1), and 260 mg (71 %) of ethanesulfonic acid (2,2-dimethyl-6-thiophen-2-yl-chroman-4-yl)methylamide were obtained as an oil.

Workup

  1. customAfter removing the solvent
  2. washwashed with water
  3. customAfter drying
  4. customremoving the solvent
  5. customthe residue obtained
  6. customwas purified by column chromatography (eluent heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-c4ab334bcda84d62b025a9f10df2642d
Source dataset
uspto-grants-2001_01
Patent number
US06177449B1

Reaction notes

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