Methyl iodide → HCID 68709761, compound

HRID 2067939Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:10](I)=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:8]([CH3:19])[N:7]=1)=[O:5])[CH3:2].[CH2:20]([Li])CCC.CI.C(OCC)(=O)C>C1COCC1.[Cl-].[Na+].O>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:20])=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:8]([CH3:19])[N:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: -75 °C

Procedure

To a −78° C. solution of 4.06 g of 5-(4-Fluoro-phenyl)-4-iodo-1-methyl-1H-pyrazole-3-carboxylic acid ethyl ester in 80 mL of dry THF were added dropwise 8.13 ml of a 1.6 M solution of n-Butyllithium in THF maintaining the temperature below −70° C. The solution was stirred for 15 min at −75° C. and 1.4 ml of Methyl iodide was added. The reaction mixture was stirred for 30 min at −75° C. and allowed to warm up to room temperature. The mixture was worked up with Ethyl acetate and brine. The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product (3.15 g) was purified by chromatography on silica gel (Heptane/Ethyl acetate 2:1). The desired product was obtained as a yellow oil (1.00 g, 35%), which solidified on standing. MS: m/e=263.1 ([M+1]+).

Workup

stirringThe reaction mixture was stirred for 30 min at −75° C.
temperatureto warm up to room temperature
dry with materialThe combined organic extracts were dried with magnesium sulfate
filtrationfiltered
customevaporated
customThe crude product (3.15 g) was purified by chromatography on silica gel (Heptane/Ethyl acetate 2:1)

Sources & evidence

ORD record: ord-e1c408a2051d41bbba4ad04228935926
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293916B2

Reaction notes

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