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

HRID 627017Notes

Reaction equation

HRID 627017 reaction equation
[C:1]([CH:4]1[N:12](C(OC(C)(C)C)=O)[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH2:5]1)(=[O:3])[NH2:2].[C:20]([OH:26])([C:22]([F:25])([F:24])[F:23])=[O:21]>C(Cl)Cl>[F:23][C:22]([F:25])([F:24])[C:20]([OH:26])=[O:21].[NH:12]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH2:5][CH:4]1[C:1]([NH2:2])=[O:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118380479tert-butyl 2-carbamoyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 1317352482,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid amide, trifluoroacetate saltYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-carbamoyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (100 mg, 380 μmol, Eq: 1.00) in DCM (3 mL) was added TFA (2 mL, 26.0 mmol, Eq: 68.3) and the resulting mixture was stirred overnight. The reaction mixture was concentrated in vacuo and azeotroped with DCM (2×10 mL). The resulting residue was triturated with ether to give 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid amide, trifluoroacetate salt as an off-white solid (95 mg)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customazeotroped with DCM (2×10 mL)
  3. customThe resulting residue was triturated with ether

Sources & evidence

ORD record
ord-e6cf0a1947e24a29a9e6b63dbdf0197a
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

Loading…