Tetrahydrofuran → HCID 58094890, compound

HRID 2402476Notes

Reaction equation

[C:1]([C:3]1[C:4]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])=[C:5]([C:15](N(OC)C)=[O:16])[S:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([F:14])[CH:9]=1)#[N:2].O1CCC[CH2:30]1.C[Li]>C(OCC)C>[C:15]([C:5]1[S:6][C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([F:14])[CH:9]=2)=[C:3]([C:1]#[N:2])[C:4]=1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[Cl:28])(=[O:16])[CH3:30]

Participants

Conditions

Temperature: -78 °C

Procedure

To a flame dried flask were placed 4-cyano-3-(2,4-dichlorophenyl)-5-(2-fluoropyridin-4-yl)-N-methoxy-N-methylthiophene-2-carboxamide (1.45 g, 3.32 mmol) and tetrahydrofuran (90 mL, 1000 mmol) under argon. The solution was cooled to −78° C. and Methyllithium (4.653 mmol, 4.653 mmol) in diethylether (1.6M) solution was added. After addition, the mixture was kept at this temperature for 30 min. The mixture was quenched by ammonium chloride solution. The mixture was extracted with EtOAc and the organic layer was collected and dried over Na2SO4. The solvent was evaporated and the residue was purified using column chromatography. The title compound was collected as a white solid (0.93 g, 71.5%). LCMS: (FA) ES+391, 393. 1H NMR (400 MHz, d1-chloroform) δ: 8.43 (1H, d, J=5.28 Hz), 7.67-7.62 (2H, m), 7.48 (1H, dd, J=8.24, 2.01 Hz), 7.38 (1H, s), 7.35 (1H, d, J=8.24 Hz), 2.13 (3H, s)

Workup

customTo a flame dried flask
additionAfter addition
customThe mixture was quenched by ammonium chloride solution
extractionThe mixture was extracted with EtOAc
customthe organic layer was collected
dry with materialdried over Na2SO4
customThe solvent was evaporated
customthe residue was purified
customThe title compound was collected as a white solid (0.93 g, 71.5%)

Sources & evidence

ORD record: ord-ae0e4f0e896048b486e8ba787864d160
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796314B2

Reaction notes

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