Methyl iodide → HCID 58827051, compound

HRID 76904Notes

Reaction equation

[CH:1]1[N:2]=[CH:3][N:4]2[CH:9]([C:10]3[C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:14][C:13]([C:22]#[N:23])=[CH:12][CH:11]=3)[CH2:8][CH2:7][CH2:6][C:5]=12.[Li+].[CH3:25][Si]([N-][Si](C)(C)C)(C)C.CI>C1COCC1>[CH3:25][C:9]1([C:10]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13]([C:22]#[N:23])=[CH:12][CH:11]=2)[N:4]2[CH:3]=[N:2][CH:1]=[C:5]2[CH2:6][CH2:7][CH2:8]1

Participants

Conditions

Temperature: -30 °C

Procedure

To a solution of 6-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)biphenyl-3-carbonitrile (53 mg, 0.177 mmol) in THF (2 mL) at −40° C. is added LHMDS (1.0 M in THF, 0.27 mL, 0.27 mmol). The resulting brown solution is stirred at −30° C. for 0.5 h. To the reaction mixture is added methyl iodide (0.017 mL, 0.272 mmol) and the mixture is warmed up to ambient temperature and stirred overnight. The reaction mixture is quenched by saturated aqueous NH4Cl and the reaction is partitioned between CH2Cl2 and brine. The organic layer is washed with brine, dried over anhydrous Na2SO4 and concentrated to give the crude oil, which is subject to flash chromatography (silica gel) eluting with MeOH:CH2Cl2 to yield the desired compound. MS (ESI) m/z 314 (M+H).

Workup

temperaturethe mixture is warmed up to ambient temperature
stirringstirred overnight
customThe reaction mixture is quenched by saturated aqueous NH4Cl
customthe reaction is partitioned between CH2Cl2 and brine
washThe organic layer is washed with brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
customto give the crude oil, which
washeluting with MeOH

Sources & evidence

ORD record: ord-4d54fef1b44f499e88ec1257000fee10
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835646B2

Reaction notes

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