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Triethylamine → 2-(5-Bromopyridin-3-yl)-2-azabicyclo[3.1.0]hex-3-ylmethyl methanesulfonate

HRID 241601
Notes
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Reaction equation

HRID 241601 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:13]([CH2:14][OH:15])[CH2:12][CH:11]3[CH:9]2[CH2:10]3)[CH:5]=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([O:15][CH2:14][CH:13]1[CH2:12][CH:11]2[CH:9]([CH2:10]2)[N:8]1[C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)(=[O:26])=[O:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67297729[2-(5-Bromopyridin-3-yl)-2-azabicyclo[3.1.0]hex-3-yl]methanol

Product 1

HCID 866749142-(5-Bromopyridin-3-yl)-2-azabicyclo[3.1.0]hex-3-ylmethyl methanesulfonateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of [2-(5-Bromopyridin-3-yl)-2-azabicyclo[3.1.0]hex-3-yl]methanol (462 mg, 2.43 mmol) in dry dichloromethane (10 mL) was added triethylamine (0.51 mL, 3.6 mmol) followed by methanesulfonyl chloride (334 mg, 2.92 mmol). The reaction mixture was gradually warmed to room temperature and stirred for 1 hour. The volatiles were removed under reduced pressure and the crude product was purified by flash column chromatography to obtain title compound of 586 mg as gummy liquid. Yield: 90%.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-3ba3678bc5f94c3eba5e6deaa328a185
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08653071B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes