HCID 57995663, compound → HCID 68733665, compound

HRID 385481Notes

Reaction equation

[CH:1]1([CH2:4][O:5][C:6]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)=[CH:10][C:9]([CH:22]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8][C:7]=2I)[CH2:3][CH2:2]1.[C:33]([Cu])#[N:34]>CN1C(=O)CCC1>[C:33]([C:7]1[CH:8]=[C:9]([CH:22]([CH2:28][CH:29]([CH3:30])[CH3:31])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:10]=[C:11]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:17]=2)[C:6]=1[O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1)#[N:34]

Participants

Conditions

Temperature: 200 °C

Procedure

To a stirred solution of ethyl 2-(6-(cyclopropylmethoxy)-5-iodo-4′-(trifluoromethyl) biphenyl-3-yl)-4-methylpentanoate (0.25 g, 0.447 mmol) in NMP (10 mL) was added CuCN (50 mg, 0.536 mmol) at RT under inert atmosphere. The reaction mixture was stirred at 200° C. temperature over a period of 2 h. After completion of starting material (by TLC), the reaction mixture was cooled to RT and extracted with EtOAc (3×20 mL). Combined organic layers were washed with water (3×15 mL), brine and dried over Na2SO4. After filtration and evaporation, the crude material was purified by column chromatography to afford ethyl 2-(5-cyano-6-(cyclopropylmethoxy)-4′-(trifluoromethyl) biphenyl-3-yl)-4-methylpentanoate (0.125 g) a solid.

Workup

temperatureAfter completion of starting material (by TLC), the reaction mixture was cooled to RT
extractionextracted with EtOAc (3×20 mL)
washCombined organic layers were washed with water (3×15 mL), brine
dry with materialdried over Na2SO4
filtrationAfter filtration and evaporation
customthe crude material was purified by column chromatography

Sources & evidence

ORD record: ord-ead9c30eaca44ec08c53310f32b12590
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367863B2

Reaction notes

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