HCID 68787685, compound → HCID 49834377, compound

HRID 1627062Notes

Reaction equation

HRID 1627062 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)=[CH:8][C:7]=1[C:21]([F:24])([F:23])[F:22]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:19])([CH3:20])[O:13]2)=[CH:8][C:7]=1[C:21]([F:22])([F:23])[F:24]

Participants

4

Reactant 1

HCID 68787685HCID 68787685, compound

Product 1

HCID 49834377HCID 49834377, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-trifluoromethyl-phenyl]-acrylic acid methyl ester (preparation 1) in ethyl acetate (200 mL) containing Pd/C (500 mg) was hydrogenated overnight at rt. The catalyst was filtered off through Celite, and the filtrate was concentrated under reduced pressure to afford the title compound as a colorless oil, which was used without further purification. 1H NMR (300 MHz, DMSO) δ 7.92-7.83 (m, 2H), 7.54 (d, 1H), 3.62 (s, 3H), 3.06 (t, 2H), 2.70-2.61 (m, 2H), 1.31 (s, 12H).

Workup

  1. filtrationThe catalyst was filtered off through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ab8e7de4a3484ad8b13dd8ba0153c3a8
Source dataset
uspto-grants-2014_07
Patent number
US08785494B2

Reaction notes

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