Triethylamine → N-(1H-pyrrolo[2,3-b]pyridin-5-yl)-nicotinamide

HRID 60109Notes

Reaction equation

HRID 60109 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([NH2:10])[CH:9]=[C:4]2[CH:3]=[CH:2]1.C(N(CC)CC)C.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1>O1CCCC1.O>[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([NH:10][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=3)[CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 82604Nicotinoyl chlorideHCID 117151871H-pyrrolo(2,3-b)pyridin-5-amine

Product 1

HCID 58368850N-(1H-pyrrolo[2,3-b]pyridin-5-yl)-nicotinamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a reaction vial, 1H-Pyrrolo[2,3-b]pyridin-5-ylamine (35, 0.1 g, 0.8 mmol) is dissolved in 7 mL of tetrahydrofuran and triethylamine (0.10 mL, 0.75 mmol) and nicotinoyl chloride (36, 0.16 g, 1.1 mmol) are added. The reaction is stirred at room temperature for 16 hours, then diluted with water and extracted 3× with ethyl acetate. The organic layers are combined and washed with brine, then dried over sodium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-bbe9653eb99d4038b11422f7a8672a79
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Reaction notes

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