Cesium carbonate → HCID 67088891, compound

HRID 1943948Notes

Reaction equation

HRID 1943948 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:12]([OH:13])=[N:11][N:10]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:31][CH:32]1[CH2:35][O:34][CH2:33]1>CN(C=O)C.O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:12]([O:13][CH2:31][CH:32]3[CH2:35][O:34][CH2:33]3)=[N:11][N:10]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:15])=[O:16])[C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 214522323-(Iodomethyl)oxetaneHCID 178427406HCID 178427406, compound

Product 1

HCID 67088891HCID 67088891, compoundYield 24.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-Nitro-1-tosyl-1H-pyrazolo[3,4-b]pyridin-3-ol (0.05 g, 0.150 mmol) was dissolved in DMF (1.5 mL). Cesium carbonate (0.146 g, 0.450 mmole) was added, and then 3-(iodomethyl)oxetane (0.030 g, 0.150 mmol; prepared according to US 2008/0021032) was added to the mixture. The mixture was stirred at room temperature for 16 hours. The mixture was then diluted with water and extracted with EtOAc (2×50 mL), and the extracts were washed with brine (1×), dried over sodium sulfate and concentrated under reduced pressure. Preparative TLC (0.5 mm plate, 1:1 ethyl acetate/hexanes) afforded 5-nitro-3-(oxetan-3-ylmethoxy)-1-tosyl-1H-pyrazolo[3,4-b]pyridine (15 mg, 19%) as a solid. 1H NMR (400 MHz, CDCl3) δ 9.54-9.52 (m, 1H), 8.83-8.81 (m, 1H), 8.05-7.99 (m, 2H), 7.34-7.28 (m, 2H), 4.93-4.86 (m, 2H), 4.78-4.72 (m, 2H), 4.62-4.55 (m, 2H), 3.57-3.48 (m, 1H), 2.40 (s, 3H).

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washthe extracts were washed with brine (1×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b9f4bb434d44f13a7f06e94ee9ef18e
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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