Dichloromethane → 3-Chloro-6-fluoro-[1,2,4]triazolo[4,3-a]pyridine
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][N:10]=2)[CH:7]=1.BrN1C(=O)CCC1=O.C(Cl)[Cl:20]>>[Cl:20][C:8]1[N:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1Participants
4
Conditions
- Temperature
- 45 °C
Procedure
Intermediate 14a (908 mg, 6.60 mmol) was dissolved in DCM (50 mL) and N-bromosuccinimide (1.29 g, 7.26 mmol) added. The reaction was heated to 45° C. for 4 h, then cooled and partitioned between DCM (150 mL) and saturated aqueous NaHCO3 (150 mL), and extracted into DCM (3×). The combined organic layers were washed with brine, dried (MgSO4) and evaporated in vacuo. Purification by FCC, using 0-5% [2M NH3 in MeOH] in DCM, gave the title compound (900 mg, 63%). LCMS (Method 1): Rt 1.94 min, m/z 216/218 [MH+].
Workup
- temperaturecooled
- custompartitioned between DCM (150 mL) and saturated aqueous NaHCO3 (150 mL)
- extractionextracted into DCM (3×)
- washThe combined organic layers were washed with brine
- dry with materialdried (MgSO4)
- customevaporated in vacuo
- customPurification by FCC
Sources & evidence
- ORD record
- ord-f5529c36dcaf4e95aa67545b3d220c5b
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359354B2
Reaction notes
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