Diisopropylethylamine → 1H-Pyrrolo[2,3-b]pyridine, 6-bromo-1-[tris(1-methylethyl)silyl]-

HRID 1098506Notes

Reaction equation

HRID 1098506 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Si:20](OS(C(F)(F)F)(=O)=O)([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22]>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 111599156-Bromo-7-azaindole

Product 1

HCID 580876901H-Pyrrolo[2,3-b]pyridine, 6-bromo-1-[tris(1-methylethyl)silyl]-

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

6-bromo-1H-pyrrolo[2,3-b]pyridine (587, 275 mg, 1.39 mmol) was dissolved in 4 mL of dry dioxane. DIEA (3 equiv) and TIPS-OTf (2.5 equiv) were added and the reaction was stirred at 50° C. overnight. The reaction was then diluted with 20 mL of ethyl acetate and washed 2 times with 10 mL NaHCO3 (aq., 5%) and once with 10 mL brine. The organic fraction was dried over MgSO4, evaporated and diluted with 5.5 mL of dry toluene 10 mg bromide per 0.2 mL of solution) to use directly in the next reaction step.

Workup

  1. washwashed 2 times with 10 mL NaHCO3 (aq., 5%)
  2. dry with materialThe organic fraction was dried over MgSO4
  3. customevaporated
  4. additiondiluted with 5.5 mL of dry toluene 10 mg bromide per 0.2 mL of solution)
  5. customto use directly in the next reaction step

Sources & evidence

ORD record
ord-26db3e664336498ab8c6b133e465834f
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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