Triphenylphosphine → 3-{3-[1-(4-chloro-phenyl)-1-phenyl-meth-(E)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester

HRID 1623436Notes

Reaction equation

HRID 1623436 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:12](=[O:21])[C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:48][C:49]1[CH:54]=[CH:53][C:52](I)=[CH:51][CH:50]=1.[F-].[Cs+]>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)/[C:13](=[C:14](\[C:52]3[CH:53]=[CH:54][C:49]([Cl:48])=[CH:50][CH:51]=3)/[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)/[C:12]2=[O:21])[CH:5]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 125101-Chloro-4-iodobenzeneHCID 25953Cesium fluorideHCID 670361553-{[Phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl ester

Product 1

HCID 510334343-{3-[1-(4-chloro-phenyl)-1-phenyl-meth-(E)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-{[phenyl-(3-phenyl-propynoyl)-amino]-methyl}-benzoic acid methyl ester (369.4 mg, 1 mmol) in THF (5 ml) were added palladium(II) acetate (11.2 mg, 0.05 mmol), triphenylphosphine (26.2 mg, 0.1 mmol), 1-chloro-4-iodobenzene (262.3 mg, 1.1 mmol) and cesium fluoride (456 mg, 3 mmol) at room temperature. The solution was stirred for 3 h at 110° C. under an argon atmosphere. After being quenched with water, the mixture was extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with (hexane/ethyl acetate=5/1) to give 3-{3-[1-(4-chloro-phenyl)-1-phenyl-meth-(E)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester, yield 297 mg (62%); 1H NMR (CDCl3, 300 MHz) δ ppm 8.00 (s, 1H), 7.92 (d, 1H), 7.50 (d, 1H), 7.26-7.43 (m, 10H), 7.08 (dt, 1H), 6.71 (dt, 1H), 6.59 (d, 1H), 6.52 (d, 1H), 4.95 (s, 2H), 3.90 (s, 3H).

Workup

  1. customAfter being quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel eluting with (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-8e3c486d900b49b499031dda37c979cd
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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