Cesium carbonate → 5-(1,1-Dimethylethyl)-6-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-1-phenyl-1H-pyrazolo[3,4-b]pyridine

HRID 1263487Notes

Reaction equation

HRID 1263487 reaction equation
[CH3:1][C:2]([C:5]1[C:10](=[O:11])[NH:9][C:8]2[N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:13]=[CH:14][C:7]=2[CH:6]=1)([CH3:4])[CH3:3].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:29][C:30]1[N:31]([CH3:35])[N:32]=[CH:33][N:34]=1>CN(C)C=O>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]2[CH:14]=[N:13][N:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:8]2=[N:9][C:10]=1[O:11][CH2:29][C:30]1[N:31]([CH3:35])[N:32]=[CH:33][N:34]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 222853325-(chloromethyl)-1-methyl-1H-1,2,4-triazole hydrochlorideHCID 1358542811,7-Dihydro-5-(1,1-dimethylethyl)-1-phenylpyrazolo[3,4-b]pyridin-6-one

Product 1

HCID 99251755-(1,1-Dimethylethyl)-6-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-1-phenyl-1H-pyrazolo[3,4-b]pyridineYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1,7-dihydro-5-(1,1-dimethylethyl)-1-phenylpyrazolo[3,4-b]pyridin-6-one (26 mg, 0.097 mmol) in dry N,N-dimethylformamide (4 ml) under nitrogen was added cesium carbonate (95 mg, 0.29 mmol) followed by 3-chloromethyl-2-methyl-2H-[1,2,4]triazole hydrochloride (25 mg, 0.15 mmol). The reaction mixture was heated at 60° C. for 17 h. The mixture was then allowed to cool and partitioned between water and diethyl ether. The aqueous phase was extracted a second time with diethyl ether and the combined organic extracts were dried (MgSO4) and concentrated to give the title compound as a white solid (25 mg, 71%), m.p. 143-145° C. δH (400 MHz; CDCl3) 1.40 (9H, s), 3.93 (2H, s), 5.69 (1H, s), 7.29-7.32 (1H, m), 7.49-7.53 (2H, m), 7.93 (1H, s), 7.98 (1H, s), 8.05 (1H, s), 8.19-8.21 (2H, m); m/z (ES+) 363 (M+H+)

Workup

  1. temperatureto cool
  2. custompartitioned between water and diethyl ether
  3. extractionThe aqueous phase was extracted a second time with diethyl ether
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-695f12025e6c4341a85a06d035b43cd3
Source dataset
uspto-grants-2003_04
Patent number
US06541484B2

Reaction notes

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