Triethylamine → HCID 68785384, compound

HRID 2266016Notes

Reaction equation

HRID 2266016 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]=[CH:6][C:7]1[C:8](Cl)=[N:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=1)[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC.[CH3:45][Si:46]([C:49]#[CH:50])([CH3:48])[CH3:47]>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.CN(C=O)C>[CH2:1]([O:3][C:4](=[O:18])[CH:5]=[CH:6][C:7]1[C:8]([C:50]#[C:49][Si:46]([CH3:48])([CH3:47])[CH3:45])=[N:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=1)[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 72335620HCID 72335620, compound

Product 1

HCID 68785384HCID 68785384, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Microwave vial was charged with 3-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid ethyl ester (103 mg, 0.368 mmol), Pd(PPh3)2Cl2 (0.06 eq), CuI (0.06 eq), PPh3 (0.2 eq), Et3N (15 eq), (trimethylsilyl)acetylene and DMF (0.25 ml). The vial was irradiated in microwave synthesizer at 120° C. for 25 min. The contents of the vial were filtered through a Celite pad, which was washed out thoroughly with EtOAc. The filtrate was evaporated, and the residue was purified by column chromatography to 3-(6-trifluoromethyl-2-trimethylsilanylethynyl-pyridin-3-yl)-acrylic acid ethyl ester (58 mg, 46%).

Workup

  1. customThe vial was irradiated in microwave synthesizer at 120° C. for 25 min
  2. filtrationThe contents of the vial were filtered through a Celite pad, which
  3. washwas washed out thoroughly with EtOAc
  4. customThe filtrate was evaporated
  5. customthe residue was purified by column chromatography to 3-(6-trifluoromethyl-2-trimethylsilanylethynyl-pyridin-3-yl)-acrylic acid ethyl ester (58 mg, 46%)

Sources & evidence

ORD record
ord-86b969d8cc2b43909e95e5dd2e7761d0
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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