Triethylamine → 1-(1H-Indazol-5-yl)ethan-1-one

HRID 1094641Notes

Reaction equation

HRID 1094641 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[CH3:11][C:12]([O:15]C(OC(OC(C)(C)C)=O)=O)(C)C.CCN(CC)CC>CC#N.CN(C1C=CN=CC=1)C.O>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([C:12](=[O:15])[CH3:11])=[CH:10][CH:9]=2)[CH:5]=[N:6]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 218947395-Iodo-1H-indazole

Product 1

HCID 391039881-(1H-Indazol-5-yl)ethan-1-one

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-iodo-1H-indazole (1.00 g, 4.10 mmol) in CH3CN (20 ml) were added Boc2O (984 mg, 4.51 mmol), DMAP (125 mg, 1.02 mmol) and Et3N (0.64 ml, 4.6 mmol). The reaction mixture was stirred at room temperature for 5 hours, diluted with H2O and extracted with AcOEt. The organic layers were dried over Na2SO4 and concentrated in vacuo to give the title compound. This compound (>1.5 g) was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 1.72 (9H, s), 7.79 (1H, d, J=8.8 Hz), 7.98 (1H, d, J=8.8 Hz), 8.10 (2H, s). MS (ESI) m/z 345 (M+H)+.

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd7e9fb7ff9847899a4bd20ca91a002f
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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