1,2-Dimethoxyethane → HCID 68784904, compound

HRID 2266007Notes

Reaction equation

HRID 2266007 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].[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].COCCOC>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.C(O)C>[CH2:1]([O:3][C:4](=[O:18])[CH:5]=[CH:6][C:7]1[C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=1)[CH3:2]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 72335620HCID 72335620, compound

Product 1

HCID 68784904HCID 68784904, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolvent

Procedure

Microwave vial was charged with 3-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid ethyl ester (100 mg, 0.376 mmol), phenylboronic acid (2 eq), Cs2CO3 (3 eq), Pd(PPh3)2Cl2 (0.08 eq), DME (1 ml), and ethanol (0.25 ml). The vial was irradiated in microwave synthesizer at 140° C. for 20 min. The contents of the vial were filtered through a celite pad, which was washed out thoroughly with methanol. The filtrate was evaporated, and the residue was purified by column chromatography to give 3-(2-phenyl-6-trifluoromethyl-pyridin-3-yl)-acrylic acid ethyl ester (96 mg, 80%).

Workup

  1. customThe vial was irradiated in microwave synthesizer at 140° C. for 20 min
  2. filtrationThe contents of the vial were filtered through a celite pad, which
  3. washwas washed out thoroughly with methanol
  4. customThe filtrate was evaporated
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-34877c9cc50e4b66b814756fd7424239
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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