Isoamyl Nitrite → HCID 86616968, compound

HRID 1865883Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8](N)=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)[N:6]=1)=[O:4].C(ON=O)CC(C)C.C[Si](C)(C)[Br:33].C(=O)(O)[O-].[Na+]>BrCBr>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([Br:33])=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)[N:6]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 6.8 g (0.022 mol) 5-amino-6-(4-trifluoromethoxy-phenyl)-pyrazine-2-carboxylic acid methyl ester in 150 ml dibromomethane was added 3.50 ml (3.052 g; 0.026 mol) isoamylnitrite. To the resulting suspension was added drop wise during 30 minutes a solution of 3.38 ml (3.38 g; 0.026 mol) trimethylbromosilane in 5 ml dibromomethane at 0° C. The mixture was stirred at 0° C. for 0.5 hours and 2 hours at room temperature. To the resulting turbid reaction mixture was added ca 150 ml of a 10% aqueous sodium bicarbonate solution with stirring. The phases were separated the organic phase was dried over magnesium sulfate, evaporated and purified by chromatography on silica gel with a gradient of 100% heptane to 10% ethyl acetate in heptane to yield 6.38 g of the title compound as off white crystalline solid. MS (ISP) (M+H+)=377.0 and 379.0.

Workup

customTo the resulting turbid reaction mixture
stirringwith stirring
customThe phases were separated the organic phase
dry with materialwas dried over magnesium sulfate
customevaporated
custompurified by chromatography on silica gel with a gradient of 100% heptane to 10% ethyl acetate in heptane

Sources & evidence

ORD record: ord-7f5bddd340214c678d2711ed341bfa42
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629346B2

Reaction notes

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