Chloroform → Ethyl (z)-[4-[3-(benzo[b]thiophen-2-yl)-3-(4-trifluoromethylphenyl)allylsulfanyl]-2-methylphenoxy]acetate

HRID 1247680Notes

Reaction equation

I/[C:2](/[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1)=[CH:3]\[CH2:4][S:5][C:6]1[CH:18]=[CH:17][C:9]([O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:8]([CH3:19])[CH:7]=1.[S:30]1[C:34]([Sn](CCCC)(CCCC)CCCC)=[CH:33][C:32]2[CH:48]=[CH:49][CH:50]=[CH:51][C:31]1=2.C(Cl)(Cl)Cl.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C1CCCCC1.[F-].[K+]>CN(C)C=O.C(OCC)(=O)C>[S:30]1[C:34](/[C:2](/[C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[CH:3]\[CH2:4][S:5][C:6]2[CH:18]=[CH:17][C:9]([O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:8]([CH3:19])[CH:7]=2)=[CH:33][C:32]2[CH:48]=[CH:49][CH:50]=[CH:51][C:31]1=2

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl (Z)-[4-[3-iodo-3-(4-trifluoromethylphenyl)allylsulfanyl]-2-methylphenoxy]acetate (407.1 mg, 0.759 mmol; example 29, step D-E) and (benzo[b]thiophen-2-yl)-tributyltin (327.2 mg, 0.773 mmol, prepared according to Morimoto et al.: J. Med. Chem. 44, 3355 (2001)) in dry N,N-dimethylformamide (3 mL) Pd2(dba)3.CHCl3 (24.1 mg, 0.023 mmol) was added. Traces of moisture and oxygen were removed and 0.20M solution of tri(tert.butyl)phosphine in cyclohexane (0.49 mL, 0.098 mmol) was added under atmosphere of nitrogen and the whole mixture was stirred at 60° C. for 5 h. The dark solution was poured into 10% aqueous solution of potassium fluoride (20 mL) and subsequently ethyl acetate (30 mL) was added. The layers were separated, the aqueous layer was washed with ethyl acetate (2×15 mL) and the collected organic layers were washed with brine (10 mL), 10% solution of potassium fluoride (20 mL), water (20 mL) and brine (20 mL). The organic solution was dried with anhydrous sodium sulfate and its evaporation gave an oil that was purified by column chromatography (silica gel Fluka 60, hexane/ethyl acetate 9:1) yielding 318.6 mg of the ester. Yield: 318.6 mg (76%).

Workup

customTraces of moisture and oxygen were removed
additionwas added
customThe layers were separated
washthe aqueous layer was washed with ethyl acetate (2×15 mL)
washthe collected organic layers were washed with brine (10 mL), 10% solution of potassium fluoride (20 mL), water (20 mL) and brine (20 mL)
dry with materialThe organic solution was dried with anhydrous sodium sulfate and its evaporation
customgave an oil that
customwas purified by column chromatography (silica gel Fluka 60, hexane/ethyl acetate 9:1)

Sources & evidence

ORD record: ord-d2ca5ce22cea43ed97ca273c940e2a14
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129268B2

Reaction notes

Loading…