Tri-o-tolylphosphine → HCID 66911576, compound

HRID 1967433Notes

Reaction equation

HRID 1967433 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]1[O:14][CH2:13][CH2:12][O:11]1.[C:15]([N:19]1[C@H:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][O:21][C:20]1=[O:30])(=[O:18])[CH:16]=[CH2:17].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:11]1[CH2:12][CH2:13][O:14][CH:10]1[C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1/[CH:17]=[CH:16]/[C:15]([N:19]1[C@H:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][O:21][C:20]1=[O:30])=[O:18]

Participants

6

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 111845031,3-Dioxolane, 2-(2-bromo-5-methoxyphenyl)-HCID 11830887HCID 11830887, compound

Product 1

HCID 66911576HCID 66911576, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of Compound 20 (2.6 g, 10.0 mmol), (R)-3-acryloyl-4-phenyloxazolidin-2-one (2.2 g, 10.0 mmol), tri-o-tolyl phosphine (0.30 g, 1.0 mmol) and palladium acetate (0.11 g, 0.5 mmol) in triethylamine (35 mL) under argon was stirred under reflux for 90 min. The resulting reaction mixture was cooled to room temperature and concentrated in vacuo. The residue obtained was purified by flash column chromatography (hexanes/ethyl acetate 95:5 to 60:40) to give Compound 21 (3.2 g, 81%) as a light yellow oil: 1H NMR (500 MHz, CDCl3) δ 8.19 (d, J=15.5 Hz, 1H), 7.81 (d, J=15.5 Hz, 1H), 7.40 (d, J=8.5 Hz, 1H), 7.41-7.30 (m, 5H), 7.17 (d, J=3.0 Hz, 1H), 6.91 (dd, J=8.5, 3.0 Hz, 1H), 6.01 (s, 1H), 5.54 (dd, J=9.0, 3.5 Hz, 1H), 4.73 (t, J=9.0 Hz, 1H), 4.30 (dd, J=9.0, 4.0 Hz, 1H), 4.32-4.28 (m, 2H), 4.13-4.10 (m, 2H), 3.85 (s, 3H).

Workup

  1. temperatureunder reflux for 90 min
  2. customThe resulting reaction mixture
  3. concentrationconcentrated in vacuo
  4. customThe residue obtained
  5. customwas purified by flash column chromatography (hexanes/ethyl acetate 95:5 to 60:40)

Sources & evidence

ORD record
ord-e875815c06f84212ac0c0dcae5026263
Source dataset
uspto-grants-2013_04
Patent number
US08420811B2

Reaction notes

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