Ammonium Chloride → (6-Bromopyridin-3-yl)methyl methanesulfonate
Reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].[Cl-].[NH4+]>ClCCl.O>[CH3:19][S:20]([O:9][CH2:8][C:5]1[CH:6]=[N:7][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:22])=[O:21]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
(6-Bromopyridin-3-yl)methanol (2.45 g, 13.0 mmol) was dissolved in dichloromethane (20 mL), cooled to 0° C. and treated successively with N,N-diisopropylethylamine (2.73 mL, 15.6 mmol, 1.2 equiv) and methanesulfonyl chloride (1.17 mL, 15.0 mmol, 1.15 equiv). After stirring for 30 minutes, the mixture was treated with ammonium chloride (10 mL, aqueous saturated) and warmed to ambient temperature. The mixture was poured into water (100 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.
Workup
- temperaturewarmed to ambient temperature
- extractionextracted with ethyl acetate (2×100 mL)
- dry with materialThe combined organic extracts were dried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-cbba3324145b413fa0356d76683a33d6
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293744B2
Reaction notes
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