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

HRID 595819Notes

Reaction equation

HRID 595819 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-4f2001d1fa314d37b4d82a09d461dd5c
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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