Methyl iodide → HCID 86685701, compound

HRID 536578Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:29])[CH:5]([CH3:28])[CH2:6][C:7]1[CH:11]=[C:10]([CH3:12])[N:9]([CH2:13][C:14]2[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:15]=2[O:21][CH2:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[N:8]=1)[CH3:2].[CH3:30]I>C1COCC1>[CH2:1]([O:3][C:4](=[O:29])[C:5]([CH3:30])([CH3:28])[CH2:6][C:7]1[CH:11]=[C:10]([CH3:12])[N:9]([CH2:13][C:14]2[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:15]=2[O:21][CH2:22][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)[N:8]=1)[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 3-{1-[5-bromo-2-(2-cyclopentylmethoxy)-benzyl]-5-methyl-1H-pyrazol-3-yl}-2-methyl-propionic acid ethyl ester (0.14 g, 0.3 mmol) in dry THF (5 ml) under a N2 atmosphere at −78° C. was added lithium bis(trimethylsislyl)amide (1.8 ml, 1M in THF). The mixture was stirred for 1 hour before addition of a THF solution (1 ml) of MeI (0.255 g, 0.18 mmol). After stirring 3 hours more at −78° C. the mixture was left at RT for 16 hours. The reaction was quenched with sat NH4Cl solution and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4) and evaporated to dryness. The residue was purified by MPLC (10 g SiO2 cartridge, eluent 95-90% iso-hexane-5-10% EtOAc) to yield 0.033 g of 3-{1-[5-bromo-2-(2-cyclopentylmethoxy)-benzyl]-5-methyl-1H-pyrazol-3-yl}-2,2-dimethyl-propionic acid ethyl ester which was converted to the title compound following the method in Example 1, Step 8.

Workup

waitwas left at RT for 16 hours
customThe reaction was quenched with sat NH4Cl solution
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried (MgSO4)
customevaporated to dryness
customThe residue was purified by MPLC (10 g SiO2 cartridge, eluent 95-90% iso-hexane-5-10% EtOAc)

Sources & evidence

ORD record: ord-8fba0d63fa7a4e21a9cdbbc36ad0191a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859606B2

Reaction notes

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