Trifluoroacetic acid → Diethyl 1-(4-aminobutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

HRID 1521709Notes

Reaction equation

HRID 1521709 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH:11]([N:13]1[C:17]2=[N:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:21]=[C:16]2[CH:15]=[C:14]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:12])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][CH:11]([N:13]1[C:17]2=[N:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:21]=[C:16]2[CH:15]=[C:14]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67238426HCID 67238426, compound

Product 1

HCID 67237898Diethyl 1-(4-aminobutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylateYield 129.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 1-{4-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (1.20 g, 2.77 mmol) in CH2Cl2 (16 mL) is added TFA (4 mL). The mixture is stirred at room temperature for 3 hr. The mixture is concentrated under reduced pressure and the residue is partitioned between ethyl acetate and saturated NaHCO3 solution. The layers are separated and the aqueous layer is further extracted with ethyl acetate. The combined organic phases are washed with brine, and are dried (Na2SO4) and concentrated in vacuo to afford the title compound (1.20 g, >99%) which is used in the next step without purification. LCMS: 334.75 (M+H+).

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customthe residue is partitioned between ethyl acetate and saturated NaHCO3 solution
  3. customThe layers are separated
  4. extractionthe aqueous layer is further extracted with ethyl acetate
  5. washThe combined organic phases are washed with brine
  6. dry with materialare dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d6d9a8074e84a3f8b15f7ed98b58041
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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