Triethylamine → tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate

HRID 45575

Reaction equation

HRID 45575 reaction equation
C[Si]([C:5]#[CH:6])(C)C.C(N(CC)CC)C.I[C:15]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[N:17]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:16]=1.[CH2:31]([N:38]=[N+:39]=[N-:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH2:31]([N:38]1[CH:6]=[C:5]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:17]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:16]=2)[N:40]=[N:39]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 12152Benzyl azideHCID 66111TrimethylsilylacetyleneHCID 23529164tert-Butyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 53496547tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

1.1 0.21 ml (1.50 mmol) of trimethylsilylacetylene and 0.28 ml (2.00 mmol) of triethylamine are added successively to a suspension, kept under argon, of 14 mg (0.02 mmol) of bis(triphenylphosphine)palladium dichloride, 8 mg (0.04 mmol) of copper(I) iodide and 344 mg (1.00 mmol) of tert-butyl 3-iodo-(1H)-pyrrolo[2,3-b]pyridine-1-carboxylate in 5 ml of THF, and the mixture is stirred at room temperature for one hour under argon. Then, for the removal of excess trimethylsilylacetylene, argon is passed through the reaction mixture for 5 minutes. 1.10 ml (1.10 mmol) of a 1 M solution of tetrabutylammonium fluoride in THF are subsequently added, and the reaction mixture is stirred at room temperature for 30 minutes. A solution of 136 mg (1.00 mmol) of benzyl azide in 1 ml of THF is then added, and the reaction mixture is stirred at room temperature for 66 hours. The reaction mixture is adsorbed onto kieselguhr and chromatographed on a silica-gel column with petroleum ether/ethyl acetate 2:1, giving tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate as yellow oil; ESI 376.

Workup

  1. customThen, for the removal of excess trimethylsilylacetylene, argon
  2. waitis passed through the reaction mixture for 5 minutes
  3. addition1.10 ml (1.10 mmol) of a 1 M solution of tetrabutylammonium fluoride in THF are subsequently added
  4. stirringthe reaction mixture is stirred at room temperature for 30 minutes
  5. stirringthe reaction mixture is stirred at room temperature for 66 hours
  6. customchromatographed on a silica-gel column with petroleum ether/ethyl acetate 2:1

Sources & evidence

ORD record
ord-1fab8d0cf8c84e5f8bc7086b44068c58
Source dataset
uspto-grants-2013_09
Patent number
US08541584B2

Linked notes

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