5-Methylisatin → HCID 135989001, compound

HRID 1615290Notes

Reaction equation

HRID 1615290 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[NH2:13][C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[N:19][NH:20]2)=[CH:16][CH:15]=1>CCO.C(O)(=O)C>[NH:20]1[C:21]2[C:17](=[CH:16][CH:15]=[C:14]([N:13]=[C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=4)[NH:7][C:6]3=[O:11])[CH:22]=2)[CH:18]=[N:19]1

Participants

5

Reactant 2

HCID 118405-MethylisatinHCID 814231H-Indazol-6-amine

Product 1

HCID 135989001HCID 135989001, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 5-methylisatin (80.5 mg, 0.5 mmol) and 6-aminoindazole (66.5 mg, 0.5 mmol) in EtOH (2 mL) was added 1 drops of acetic acid. The resulting mixture was capped and microwaved 30 min at 120° C. After cooling to rt, it was stirred for 5 min at rt and the resulting precipitate was collected by suction filtration to give the title compound (35 mg, 28%) as an orange red solid. 1H NMR indicated a 80:20 mixture of E/Z isomers. 1H NMR (400 MHz, DMSO-d6) δ 13.03 (s, 1H, NH), 10.89 (s, 1H, NH), 8.10 (s, 1H), 7.84 (d, J=8.8 Hz, 1H), 7.15 (d, J=7.2 Hz, 1H), 7.07 (s, 1H), 6.81-6.74 (m, 2H), 6.17 (s, 1H), 2.49 (s, 3H, CH3); MS ESI 277.0 [M+H]+, calcd for [C16H12N4O+H]+ 277.1.

Workup

  1. customThe resulting mixture was capped
  2. custommicrowaved 30 min at 120° C
  3. filtrationthe resulting precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-0cf686ae1c46422aaa85f53079b45016
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…