Triethylamine → (4-Acetoxy-6-fluoro-3-trimethylsilanylethynyl-naphthalen-2-yl)-acetic acid methyl ester

HRID 238641Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[C:14](I)=[C:13]([O:16][C:17](=[O:19])[CH3:18])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:20])[CH:11]=2)[CH:6]=1.C(N(CC)CC)C.[CH3:29][Si:30]([C:33]#[CH:34])([CH3:32])[CH3:31]>CN(C)C=O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[C:14]([C:34]#[C:33][Si:30]([CH3:32])([CH3:31])[CH3:29])=[C:13]([O:16][C:17](=[O:19])[CH3:18])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:20])[CH:11]=2)[CH:6]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of (4-acetoxy-6-fluoro-3-iodo-naphthalen-2-yl)acetic acid methyl ester (300 mg, 0.75 mmol) and triethylamine (3 mL) in N,N-dimethylformamide (3 mL), was added bis(triphenylphosphine)dichloropalladium(II) (53 mg, 0.075 mmol), copper iodide (42 mg, 0.229 mmol) and trimethylsilanylacetylene (108 mg, 1.12 mmol) under an argon atmosphere. After being heated at 150° C. for 6 minutes with microwave irradiation, the resulting mixture was cooled, diluted with ethyl acetate (20 mL), and washed with brine (15 mL×2). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column (elution with 10% ethyl acetate in petroleum ether) to afford (4-acetoxy-6-fluoro-3-trimethylsilanylethynyl-naphthalen-2-yl)-acetic acid methyl ester (208 mg, 75%) as a light yellow solid.

Workup

temperaturethe resulting mixture was cooled
washwashed with brine (15 mL×2)
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by flash column (elution with 10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-02522059d1f24a22adafe5a74d46d339
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642629B2

Reaction notes

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