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

HRID 238641
Notes
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Reaction equation

HRID 238641 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 59326600(4-Acetoxy-6-fluoro-3-iodo-naphthalen-2-yl)acetic acid methyl ester

Product 1

HCID 59326569(4-Acetoxy-6-fluoro-3-trimethylsilanylethynyl-naphthalen-2-yl)-acetic acid methyl esterYield 75%

Reagents, catalysts & solvents 4

HCID 83717
Copper iodide
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

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

  1. temperaturethe resulting mixture was cooled
  2. washwashed with brine (15 mL×2)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes