Trifluoroacetic acid → 3-Bromo-5-(pyrrolidin-3-yl)pyridin-2-amine

HRID 595818Notes

Reaction equation

HRID 595818 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)=[CH:4][C:3]=1[Br:20].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:20][C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118045605Tert-butyl 3-(6-amino-5-bromopyridin-3-yl)pyrrolidine-1-carboxylate

Product 1

HCID 1180452883-Bromo-5-(pyrrolidin-3-yl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 3-(6-amino-5-bromopyridin-3-yl)pyrrolidine-1-carboxylate (65 mg, 0.171 mmol) in DCM (2.4 mL) was added TFA (0.6 mL, 7.79 mmol). The reaction mixture was stirred at room temperature for 45 min. The reaction mixture was evaporated in vacuo after dilution with toluene. The crude product was used for next step without purification. The crude yield was quantitative. LCMS (m/z): 242.1/244.1 (MH+), 0.214 min.

Workup

  1. customThe reaction mixture was evaporated in vacuo after dilution with toluene
  2. customThe crude product was used for next step without purification
  3. customThe crude yield
  4. custom242.1/244.1 (MH+), 0.214 min.

Sources & evidence

ORD record
ord-04113b0eb5ad4b289d34ce7c7f3e1272
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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