Hydrogen Sulfide → HCID 178491226, compound

HRID 490092Notes

Reaction equation

C(C1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](CC1C=CC(OC)=CC=1)[N:7]=[C:6]2[CH3:21])#N.C([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])C.N1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[SH2:35].C([O:39][CH2:40]C)(=O)C>>[CH3:40][O:39][C:32]1[CH:33]=[CH:34][C:28]([CH2:27][N:24]=[C:25]([C:26]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][N:7]=[C:6]3[CH3:21])[SH:35])=[CH:30][CH:31]=1

Participants

Reactant 4

HCID 402Hydrogen Sulfide

HCID 8857Ethyl Acetate

HCID 22561186Pyridine triethylamine

HCID 689992085-cyano-N-(4-methoxybenzyl)-3-methylindazole

Product 1

HCID 178491226HCID 178491226, compound

Procedure

To a solution of 5-cyano-N-(4-methoxybenzyl)-3-methylindazole 106 (0.25 g, 0.903 mmol) in 10% v/v triethylamine-pyridine (10 mL) was bubbled hydrogen sulfide gas for 10 minutes. The reaction mixture was stirred at room temperature for 16 hours. Ethyl acetate (100 mL) was added and the organic layer was washed with water, 1% aqueous citric acid and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure to yield N-(4-methoxybenzyl)-3-methylindazole-5-carboximidothioic acid 107 which was used in the next step without further purification.

Workup

washthe organic layer was washed with water, 1% aqueous citric acid and brine
dry with materialThe organic layer was dried over sodium sulfate
customThe organic solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-24d66aa78e084400a3003ed46a81d3c7
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528132B2

Reaction notes

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