Nitrogen → 3,5-Dimethyl-4-(1-oxo-indan-4-ylsulfanyl)-benzonitrile

HRID 625711Notes

Reaction equation

HRID 625711 reaction equation
[SH:1][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.Br[C:55]1[C:62]([CH3:63])=[CH:61][C:58]([C:59]#[N:60])=[CH:57][C:56]=1[CH3:64].C(N(C(C)C)CC)(C)C.N#N>O1CCOCC1>[CH3:64][C:56]1[CH:57]=[C:58]([CH:61]=[C:62]([CH3:63])[C:55]=1[S:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11])[C:59]#[N:60]

Participants

7

Reactant 5

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 110850704-Bromo-3,5-dimethyl-benzonitrileHCID 552973184-Mercapto-2,3-dihydro-1H-inden-1-one

Product 1

HCID 1180937333,5-Dimethyl-4-(1-oxo-indan-4-ylsulfanyl)-benzonitrileYield 87.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

4-Mercapto-indan-1-one (Step 1, 210 mg, 1.28 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (74 mg, 0.13 mmol), 4-bromo-3,5-dimethyl-benzonitrile (269 mg, 1.28 mmol) and diisopropylethylamine (0.88 mL, 5.1 mmol) are dissolved in 1,4-dioxane (2 mL). The mixture is degassed with N2, tris(dibenzylideneacetone)palladium(0) (117 mg, 0.13 mmol) 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: 330 mg). LC (METHOD 5): tR=1.36 min; Mass spectrum (ES+): m/z=294 [M+H]+.

Workup

  1. additionadded
  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-025797879aef413bb6456330b55491ca
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Reaction notes

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