Dimethylacetamide → HCID 86724009, compound

HRID 1475415Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:12])([CH3:11])[CH2:7][NH:8]2)=[CH:4][C:3]=1[CH3:13].C[C:15]([N:17](C)C)=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].[Zn]>[CH3:11][C:6]1([CH3:12])[C:5]2[C:9](=[CH:10][C:2]([C:15]#[N:17])=[C:3]([CH3:13])[CH:4]=2)[NH:8][CH2:7]1

Participants

Conditions

Temperature: 150 °C

Procedure

6-Bromo-3,3,5-trimethyl-2,3-dihydro-1H-indole (1.0 g, 4.17 mmol), zinc cyanide (0.563 g, 4.79 mmol), tris(dibenzylideneacetone)dipalladium (0.094 g, 0.42 mmol), 1,1′-bisdiphenylphosphino)ferrocene (0.462 g, 0.83 mmol) and powdered zinc (0.054 g, 0.83 mmol) were combined and dissolved in dimethylacetamide (20.8 mL). The reaction was degassed under nitrogen for 5 minutes, then heated with microwave irradiation for 30 minutes at 150° C. The reaction was cooled to room temperature and water was added. The mixture was extracted with diethyl ether (3×). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Chromatography (silica gel, gradient elution, 0-20%, EtOAc in petrol 40-60), gave the title compound (110 mg) MS: [M+H]+=185.

Workup

customThe reaction was degassed under nitrogen for 5 minutes
temperatureThe reaction was cooled to room temperature
additionwater was added
extractionThe mixture was extracted with diethyl ether (3×)
dry with materialThe combined organic extracts were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
washChromatography (silica gel, gradient elution, 0-20%, EtOAc in petrol 40-60)

Sources & evidence

ORD record: ord-63decbddeb9642db9d446ea16ad32638
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018214B2

Reaction notes

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