Nitrogen → 4-Mercapto-2,3-dihydro-1H-inden-1-one

HRID 625710Notes

Reaction equation

HRID 625710 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C([O-])(=[S:56])C.C(N(C(C)C)CC)(C)C.N#N>O1CCOCC1>[SH:56][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11]

Participants

7

Reactant 5

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 987131-Indanone, 4-bromo-HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 178476994HCID 178476994, compound

Product 1

HCID 552973184-Mercapto-2,3-dihydro-1H-inden-1-oneYield 54%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

4-Bromo-indanone (500 mg, 2.37 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (137 mg, 0.24 mmol), thioacetate (541 mg, 4.74 mmol) and diisopropylethylamine (1.64 mL, 5.69 mmol) are dissolved in 1,4-dioxane (2 mL). The mixture is degassed with N2 and tris(dibenzylideneacetone)palladium(0) (217 mg, 0.24 mmol) is added and heated under microwave irradiation at 120° C. for 2 hours. The solution is concentrated under vacuum. The crude product obtained is purified by flash chromatography (10-80% ethyl acetate in cyclohexane) to give the title compound (Yield: 210 mg). LC (METHOD 5): tR=0.89 min; Mass spectrum (ES−): m/z=163 [M−H]−.

Workup

  1. additionis added
  2. concentrationThe solution is concentrated under vacuum
  3. customThe crude product obtained
  4. customis purified by flash chromatography (10-80% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-7a1236e4c1254a53bf10626b4ee62280
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Reaction notes

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