Methyl chloroformate → Methyl 3-(6-amino-5-bromopyridin-3-yl)pyrrolidine-1-carboxylate

HRID 595819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595819
[Br:1][C:2]1[C:3]([NH2:13])=[N:4][CH:5]=[C:6]([CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:7]=1.CCN(C(C)C)C(C)C.Cl[C:24]([O:26][CH3:27])=[O:25]>C(Cl)Cl>[NH2:13][C:3]1[N:4]=[CH:5][C:6]([CH:8]2[CH2:12][CH2:11][N:10]([C:24]([O:26][CH3:27])=[O:25])[CH2:9]2)=[CH:7][C:2]=1[Br:1]

Komponenten

5

Edukt 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 1180452883-Bromo-5-(pyrrolidin-3-yl)pyridin-2-amine

Produkt 1

HCID 118045886Methyl 3-(6-amino-5-bromopyridin-3-yl)pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 3-bromo-5-(pyrrolidin-3-yl)pyridin-2-amine, (20 mg, 0.083 mmol) in DCM in ice bath was added DIEA (43.3 μl, 0.248 mmol) and methyl chloroformate (6.40 μl, 0.083 mmol). The reaction mixture was stirred in ice bath for 30 min. The reaction mixture was partitioned between DCM and water. The DCM layer was separated and washed with brine, dried over sodium sulfate, filtered off, and evaporated. The crude product was used for next step without purification. LCMS (m/z): 300.0, 302.0 (MH+), 0.421 min.

Aufarbeitung

  1. customThe reaction mixture was partitioned between DCM and water
  2. customThe DCM layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered off
  6. customevaporated
  7. customThe crude product was used for next step without purification
  8. custom300.0, 302.0 (MH+), 0.421 min.

Quellen und Nachweise

ORD-Eintrag
ord-4f2001d1fa314d37b4d82a09d461dd5c
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242996B2

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