Sodium Thiosulfate → (3-Bromo-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)methanol
Reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14]([CH2:16][OH:17])[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.C1C(=O)N([Br:25])C(=O)C1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(#N)C>[Br:25][C:13]1[N:9]2[N:10]=[CH:11][CH:12]=[C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[C:8]2=[N:15][C:14]=1[CH2:16][OH:17]Participants
5
Conditions
- Temperature
- -10 °C
Procedure
A suspension of compound 5d (1.0 g, 4.3 mmol) in acetonitrile (100 mL) was stirred at −10° C. (in an ice/salt water bath) for 10 min, followed by addition of NBS (0.68 g, 3.8 mmol) in acetonitrile (20 mL) dropwise via an additional funnel. After the mixture was stirred in the ice-water bath for 2 h, 5% Na2S2O3 solution (10 mL) was added to quench the reaction. The aqueous layer was extracted with DCM (2×100 mL). The combined organic layers were washed with brine, and dried over Na2SO4. The mixture was filtered, and the filtrate was concentrated to leave compound 14a as a white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C11H13BrN4O2: 313.0 (M+H). found: 313.1.
Workup
- customto quench
- customthe reaction
- extractionThe aqueous layer was extracted with DCM (2×100 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-7682167516c245029c75e474fe726b58
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193736B2
Reaction notes
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