Isatin → HCID 135988993, compound

HRID 1615289Notes

Reaction equation

HRID 1615289 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[NH2:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[N:18][NH:19]2)=[CH:15][CH:14]=1>CCO.C(O)(=O)C>[NH:19]1[C:20]2[C:16](=[CH:15][CH:14]=[C:13]([N:12]=[C:4]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:1][C:2]3=[O:3])[CH:21]=2)[CH:17]=[N:18]1

Participants

5

Reactant 2

HCID 7054IsatinHCID 814231H-Indazol-6-amine

Product 1

HCID 135988993HCID 135988993, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

To a mixture of isatin (147 mg, 1 mmol) and 6-aminoindazole (133 mg, 1 mmol) in EtOH (5 mL) was added 2 drops of acetic acid. The resulting mixture was capped and microwaved 60 min at 120° C. After cooling to rt, the precipitate was collected by suction filtration to give 135 mg (48%) of title compound as yellow solid. 1H NMR indicated a 85:15 mixture of E/Z isomers. 1H NMR (400 MHz, DMSO-d6) δ 13.04 (s, 1H, NH), 11.00 (s, 1H, NH), 8.09 (s, 1H), 8.36 (d, J=8.4 Hz, 1H), 7.32 (t, J=8.0 Hz, 1H), 7.07 (s, 1H), 6.89 (t, J=8.0 Hz, 1H), 7.77 (d, J=8.4 Hz, 1H), 6.66 (t, J=7.6 Hz, 1H), 6.32 (d, J=7.6 Hz, 1H); MS ESI 263.0 [M+H]+, calcd for [C15H10N4O+H]+ 263.1.

Workup

  1. customThe resulting mixture was capped
  2. custommicrowaved 60 min at 120° C
  3. filtrationthe precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-9cbc4c42f6974cf28def1381ea4ff0a0
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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