Methanesulfonyl chloride → 3-Bromo-5-(1-(methylsulfonyl)pyrrolidin-3-yl)pyridin-2-amine

HRID 595820Notes

Reaction equation

HRID 595820 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.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[Br:1][C:2]1[C:3]([NH2:13])=[N:4][CH:5]=[C:6]([CH:8]2[CH2:12][CH2:11][N:10]([S:24]([CH3:23])(=[O:26])=[O:25])[CH2:9]2)[CH:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 1180452883-Bromo-5-(pyrrolidin-3-yl)pyridin-2-amine

Product 1

HCID 1180455673-Bromo-5-(1-(methylsulfonyl)pyrrolidin-3-yl)pyridin-2-amine

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 (57.7 μl, 0.330 mmol) and methanesulfonyl chloride (7.08 μl, 0.091 mmol). The reaction mixture was stirred in ice bath 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 and evaporated. The crude product was used for next step without purification. LCMS (m/z): 320.0/322.0 (MH+), 0.363 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
  6. customevaporated
  7. customThe crude product was used for next step without purification
  8. custom320.0/322.0 (MH+), 0.363 min.

Sources & evidence

ORD record
ord-d28dfc69b41442eab8c81176aa824a16
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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