Tetrahydrofuran → HCID 67293404, compound

HRID 1038849Notes

Reaction equation

[H-].[Na+].C1COCC1.[CH3:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=2)[NH:11][N:10]=1.[CH3:21][Si:22]([CH2:25][CH2:26][O:27][CH2:28]Cl)([CH3:24])[CH3:23]>CCOC(C)=O.O>[CH3:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=2)[N:11]([CH2:28][O:27][CH2:26][CH2:25][Si:22]([CH3:24])([CH3:23])[CH3:21])[N:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A flask was charged with NaH (60% dispersion in mineral oil, 0.325 g, 13.6 mmol) and THF (40 mL). The mixture was cooled to about 0° C. followed by the addition of 3-methyl-6-nitro-1H-indazole (2.00 g, 11.3 mmol, ArkPharm). The mixture was stirred for about 30 min followed by the addition of SEMCl (2.26 g, 13.6 mmol). The mixture was warmed to rt and stirred for about 12 h. Water (5 mL) and EtOAc (70 mL) were added and the layers were separated. The organic layer was concentrated under reduced pressure to give 3-methyl-6-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (3.2 g, 91%): LC/MS (Table 2, Method f) Rt=2.18 min; MS m/z: 308 (M+H)+.

Workup

temperatureThe mixture was warmed to rt
stirringstirred for about 12 h
customthe layers were separated
concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-24d2355ed6904f57a60d94acc92c0712
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551981B2

Reaction notes

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