Water → HCID 9819380, compound

HRID 1797182Notes

Reaction equation

HRID 1797182 reaction equation
[F:1][C:2]([C:12]1[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6].[S:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.C1C=CC=C(B(O)O)C=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.O>[F:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([C:21]2[CH:22]=[CH:23][S:19][CH:20]=2)=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 9800265[2-Fluoro-2-(4-iodophenyl)propyl][(methylethyl)sulfonyl]amineHCID 22176598HCID 22176598, compound

Product 1

HCID 9819380HCID 9819380, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

Scheme VI, Step A′: Into a 50 mL single neck [2-fluoro-2-(4-iodophenyl)propyl][(methylethyl)sulfonyl]amine (150 mg, 0.39 mmol, prepared in example 1), thiophene-3-benzene boronic acid (74 mg, 0.56 mmol), potassium carbonate (80 mg, 0.56 mmol) and tetrakis(triphenyl phosphine)palladium(0) (31 mg, 0.027 mmol) were combined in dioxane/water (15 mL, 3:1). The mixture was heated at 100° C. under stirring for 18 hours. The reaction was cooled to room temperature and poured into H2O. The desired product was extracted with ethyl acetate and the organic layer was separated and washed twice with H2O, dried over K2CO3, and concentrated under reduced vacuum to yield the crude material (236 mg) as a dark oil. The resulting oil was purified via silica gel chromatography employing the Chromatotron using a 4000 micron rotor and eluting with a solvent of hexane/ethyl acetate 7:3 to yield the title compound (107 mg, 81%) as a white solid. Ion spray M.S. 340.0 (M*−1).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThe desired product was extracted with ethyl acetate
  3. customthe organic layer was separated
  4. washwashed twice with H2O
  5. dry with materialdried over K2CO3
  6. concentrationconcentrated under reduced vacuum
  7. customto yield the crude material (236 mg) as a dark oil
  8. customThe resulting oil was purified via silica gel chromatography
  9. washeluting with a solvent of hexane/ethyl acetate 7:3

Sources & evidence

ORD record
ord-16608b72f4714aa4b0c92d9948da3d3d
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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