Trifluoroacetic acid → N-(2,6-difluorophenyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 627051Notes

Reaction equation

HRID 627051 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]([CH:12]1[N:20](C(OC(C)(C)C)=O)[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH2:13]1)=[O:11].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[NH:9][C:10]([CH:12]1[NH:20][C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118380511tert-butyl 2-(2,6-difluorophenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 117872809N-(2,6-difluorophenyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamideYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(2,6-difluorophenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (0.2 g, 533 μmol, Eq: 1.00) in DCM (2 mL) was added TFA (2 mL, 26.0 mmol, Eq: 48.7) and the resulting solution was stirred at rt for 2 h. The reaction mixture was concentrated in vacuo and the residue was treated with saturated aqueous NaHCO3 (10 mL). The resulting mixture was extracted with DCM (3×10 mL) and the combined organic layers were dried over Na2SO4 and concentrated in vacuo to give N-(2,6-difluorophenyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide as an off-white solid (0.15 g), m/z=276 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was treated with saturated aqueous NaHCO3 (10 mL)
  3. extractionThe resulting mixture was extracted with DCM (3×10 mL)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-951c7461bebd48bc921dfe17ed1a5d23
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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