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

HRID 1626006
Notes
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Reaction equation

HRID 1626006 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 803631-(Trimethylsilyl)prop-1-yneHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 401518975-Bromo-3-iodo-4-methylpyridin-2-amine

Product 1

HCID 670776815-Bromo-3,4-dimethyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 6228DimethylformamideSolvent

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

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

Sources & evidence

ORD record
ord-fb74b887dfaf48ffb0bb0e3d14084ed4
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785438B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes