Triphenylphosphine → HCID 67036257, compound

HRID 1623483Notes

Reaction equation

HRID 1623483 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2I)[C:12](=[O:18])[C:13]#[C:14][CH:15]([CH3:17])[CH3:16])[CH:5]=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F-].[Cs+]>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13](=[C:14]([C:31]3[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=3)[CH:15]([CH3:17])[CH3:16])[C:12]2=[O:18])[CH:5]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 25953Cesium fluorideHCID 742994-Chlorophenylboronic acidHCID 67036178HCID 67036178, compound

Product 1

HCID 67036257HCID 67036257, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-{[(2-iodo-phenyl)-(4-methyl-pent-2-ynoyl)-amino]-methyl}-benzoic acid methyl ester (0.93 g, 2.02 mmol), 4-chlorophenylboronic acid (0.63 g, 4.04 mmol), triphenylphosphine (53 mg, 0.202 mmol), palladium acetate (23 mg, 0.10 mmol) and cesium fluoride (0.92 g, 6.06 mmol) in THF (15 ml) was stirred for 3 hours at 60° C. After removal of solvent, the residue was purified by flash chromatography, eluting with ethyl acetate/hexane=1:5 to afford the product 3-{3-[1-(4-chloro-phenyl)-2-methyl-propylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester (0.40 g, 44%) as a yellow solid. MS calcd. for C27H24ClNO3 445.5, obsd. (ESI+) [(M+H)+] 446.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (d, J=6.82 Hz, 6H) 3.91 (s, 3H) 4.99 (dt, J=13.71, 6.92 Hz, 1H) 5.06 (s, 2H) 5.73 (d, J=7.58 Hz, 1H) 6.62 (t, J=7.71 Hz, 1H) 6.73 (d, J=7.83 Hz, 1H) 7.05 (t, J=7.71 Hz, 1H) 7.19 (d, J=8.34 Hz, 2H) 7.46 (t, J=7.83 Hz, 1H) 7.55 (d, J=8.08 Hz, 3H) 7.94 (d, J=7.58 Hz, 1H) 8.02 (s, 1H) MS calcd. for C27H24ClNO3 445.5, obsd. (ESI+) [(M+H)+] 446.0.

Workup

  1. customAfter removal of solvent
  2. customthe residue was purified by flash chromatography
  3. washeluting with ethyl acetate/hexane=1:5

Sources & evidence

ORD record
ord-fc492f49208a466ba4649c79aaa10620
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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