Trifluoroacetic acid → 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethylamide

HRID 627014Notes

Reaction equation

HRID 627014 reaction equation
[CH2:1]([NH:3][C:4]([CH:6]1[N:14](C(OC(C)(C)C)=O)[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH2:7]1)=[O:5])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([NH:3][C:4]([CH:6]1[NH:14][C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118380480tert-butyl 2-(ethylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 1178716692,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethylamideYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 mL round-bottomed flask, tert-butyl 2-(ethylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (402 mg, 1.38 mmol, Eq: 1.00) was combined with DCM (8 mL) to give a colorless solution. TFA (2 mL, 26.0 mmol, Eq: 18.8) was added and the reaction was stirred at rt for 6 h. The reaction mixture was concentrated in vacuo, saturated aqueous NaHCO3 (30 mL) was added and the resulting mixture was extracted with DCM (20 mL×3). The organic layers were dried over Na2SO4 and concentrated in vacuo to give 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethylamide as an off-white solid (210 mg), m/z=192 (M+H).

Workup

  1. customto give a colorless solution
  2. concentrationThe reaction mixture was concentrated in vacuo, saturated aqueous NaHCO3 (30 mL)
  3. additionwas added
  4. extractionthe resulting mixture was extracted with DCM (20 mL×3)
  5. dry with materialThe organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b729dc8319fa4e3390199655abd4d47d
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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