Sodium borohydride → HCID 178503601, compound

HRID 1261975Notes

Reaction equation

Cl[C:2]1[C:7]2=[CH:8][C:9]3[C:14]([N:6]2[N:5]=[C:4]([S:15][CH3:16])[N:3]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[BH4-].[Na+]>C(O)(C)C>[CH3:16][S:15][C:4]1[NH:3][CH2:2][C:7]2=[CH:8][C:9]3[C:14]([N:6]2[N:5]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

Conditions

Temperature: 55 °C

Procedure

4-Chloro-2-methylsulfanyl-[1,2,4]triazino[1,6-a]indole (1.00 g, 4.00 mmol) was suspended in isopropyl alcohol (13 mL) at room temperature. Sodium borohydride (0.318 g, 8.41 mmol) was added and the reaction mixture was heated at 55° C. for 3 hours. The reaction was allowed to cool to room temperature, then aqueous NaHCO3/dichloromethane extraction work-up, drying and evaporation of solvent afforded 2-methylsulfanyl-3,4-dihydro-[1,2,4]triazino[1,6-a]indole. 1H-NMR (CDCl3) δ 7.63 (d, J=8.1 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.18 (m, 1H), 7.08 (m, 1H), 6.15 (s, 1H), 4.73 (s, 2H), 4.63 (br s, 1H), 2.60 (s, 3H); LC/MS (ESI+): 218.5 (M+H). Benzene (30 mL) was added, and the solution was treated with manganese(IV) oxide (1.39 g, 16.0 mmol). The reaction mixture was stirred overnight. The solids were removed by filtration through Celite and were washed with dichloromethane. The solvent was removed under vacuum to afford 2-methylsulfanyl-[1,2,4]triazino[1,6-a]indole (0.79 g, 92% over two steps), which was used in the next step without further purification. 1H-NMR (CDCl3) δ 9.05 (s, 1H), 8.15 (dd, J=8.5, 0.8 Hz, 1H), 7.86 (d, J=8.2 Hz, 1H), 7.47 (m, 1H), 7.39 (m, 1H), 6.99 (s, 1H), 2.68 (s, 3H); LC/MS (ESI+): 216.5 (M+H).

Workup

temperatureto cool to room temperature
extractionaqueous NaHCO3/dichloromethane extraction work-up
customdrying
customevaporation of solvent

Sources & evidence

ORD record: ord-58fa25f484b4432086ed44acbb7d19df
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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