1-(Trimethylsilyl)prop-1-yne → 5-Bromo-3,4-dimethyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2088971Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH3:10])=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.C([O-])(=O)C.[K+].[Cl-].[Li+].[CH3:18][Si:19]([CH3:24])([CH3:23])[C:20]#[C:21][CH3:22]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]2[C:21]([CH3:22])=[C:20]([Si:19]([CH3:24])([CH3:23])[CH3:18])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

The compound obtained in step 1 of Example 36 (1.8 g) was dissolved in N,N-dimethylformamide (40 ml), and potassium acetate (1.7 g) and lithium chloride (0.3 g) were added. After replacing the atmosphere in the system with nitrogen, palladium acetate (0.13 g) and 1-trimethylsilyl-1-propyne (4.3 ml) were added and the mixture was stirred at 90° C. for three days. The reaction solution was cooled to room temperature and then N,N-dimethylformamide was distilled off. The resulting residue was diluted with ethyl acetate and then washed with brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated to give the crude title compound (2.4 g).

Workup

additionwere added
temperatureThe reaction solution was cooled to room temperature
distillationN,N-dimethylformamide was distilled off
additionThe resulting residue was diluted with ethyl acetate
washwashed with brine
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customthe solvent was evaporated

Sources & evidence

ORD record: ord-2c6d41755b0f471d968288d0cc8b4c4a
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436012B2

Reaction notes

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