Phenylsilane → HCID 178472484, compound

HRID 2401147Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[N:19](CC=C)[C:18]([O:23][C@H:24]3[CH2:29][CH2:28][C@H:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]3)=[N:17][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([C:15]#[N:16])[CH:9]=1.C1([SiH3])C=CC=CC=1>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:19][C:18]([O:23][C@H:24]3[CH2:25][CH2:26][C@H:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:28][CH2:29]3)=[N:17][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([C:15]#[N:16])[CH:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of ethyl trans-4-{[6-chloro-5-(3-cyano-4-fluorophenyl)-1-(prop-2-en-1-yl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy}cyclohexanecarboxylate (980 mg, 2.029 mmol) in DMSO (4 mL) was added 1,1′-bis(diphenylphosphinoferrocene-Palladium (II) dichloride dichloromethane complex (148 mg, 0.203 mmol) followed by phenylsilane (220 mg, 2.029 mmol). The reaction was heated at 90° C. for 1 h. The reaction was then cooled, quenched with citric acid (10% w/v, 5 mL) and then extracted with EtOAc (2×10 mL). The organic layers were collected, dried and then concentrated in vacuo. The residue was purified via flash chromatography (40 g column, 40 mL/min flow, 0-100% EtOAc/hexane to afford ethyl trans-4-{[6-chloro-5-(3-cyano-4-fluorophenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy}-cyclohexanecarboxylate as a yellow foam.

Workup

temperatureThe reaction was then cooled
customquenched with citric acid (10% w/v, 5 mL)
extractionextracted with EtOAc (2×10 mL)
customThe organic layers were collected
customdried
concentrationconcentrated in vacuo
customThe residue was purified via flash chromatography (40 g column, 40 mL/min flow, 0-100% EtOAc/hexane

Sources & evidence

ORD record: ord-6b52ad9f14044374bfcf0257fe369781
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796258B2

Reaction notes

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