Potassium Carbonate → Methyl 3-(4-amino-1H-indazol-1-yl)benzoate

HRID 418769

Reaction equation

[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([NH2:10])[C:4]=2[CH:3]=[N:2]1.I[C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I>[NH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[N:2][N:1]2[C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

Conditions

Temperature: 100 °C

Procedure

1H-Indazol-4-amine (81 mg, 0.61 mmol) and methyl 3-iodobenzoate (160 mg, 0.61 mmol) were dissolved in DMF (1 mL) in a microwave tube. Copper (I) iodide (23 mg, 0.12 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (34 mg, 0.24 mmol) and potassium carbonate (169 mg, 1.22 mmol) were added and the mixture heated by microwave (250 W) at 100° C. for 20 minutes. The mixture was filtered through a cartridge, washing with DCM (5 mL) and the filtrate was evaporated to dryness and purified by mass-directed autopreparation. The appropriate fractions were evaporated, dissolved in DCM (10 mL), washed with aqueous sodium bicarbonate, and evaporated to give the title compound (32.7 mg).

Workup

filtrationThe mixture was filtered through a cartridge
washwashing with DCM (5 mL)
customthe filtrate was evaporated to dryness
custompurified by mass-directed autopreparation
customThe appropriate fractions were evaporated
dissolutiondissolved in DCM (10 mL)
washwashed with aqueous sodium bicarbonate
customevaporated

Sources & evidence

ORD record: ord-49835de71d8e4a398c0073584e70f4e4
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093281B2

Linked notes

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