Triethylamine → HCID 70024581, compound

HRID 1265169Notes

Reaction equation

HRID 1265169 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[C:30]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])(=[O:33])[CH:31]=[CH2:32].Br[C:40]1[CH:41]=[C:42]([CH2:61][CH2:62][C:63]([O:65][CH3:66])=[O:64])[C:43]2[CH2:44][CH2:45][CH:46]([NH:50][S:51]([C:54]3[CH:59]=[CH:58][C:57]([Cl:60])=[CH:56][CH:55]=3)(=[O:53])=[O:52])[CH2:47][C:48]=2[CH:49]=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:60][C:57]1[CH:56]=[CH:55][C:54]([S:51]([NH:50][CH:46]2[CH2:47][C:48]3[C:49]([CH:32]=[CH:31][C:30]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:40][CH:41]=[C:42]([CH2:61][CH2:62][C:63]([O:65][CH3:66])=[O:64])[C:43]=3[CH2:44][CH2:45]2)(=[O:53])=[O:52])=[CH:59][CH:58]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 80271Tri-o-tolylphosphineHCID 18614891HCID 18614891, compound

Product 1

HCID 70024581HCID 70024581, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

1.25 g (4 mmol) of tri-o-tolylphosphine, 8.5 ml of triethylamine, 230 mg (1 mmol) of palladium acetate and 9 ml of tert-butyl acrylate are added to a solution of 10 g (20.5 mmol) of methyl 3-(3-bromo-6-{[(4-chlorophenyl)sulphonyl]amino}-5,6,7,8-tetra-hydro-1-naphthyl)propanoate, described in Application EP 864 561, in 250 ml of DMF. The reaction mixture is stirred at 110° C. for 8 hours. The solvent is then evaporated off, and purification by chromatography on silica gel, using as eluant a cyclohexane/ethyl acetate mixture (80/20), yields the expected product.

Workup

  1. customThe solvent is then evaporated off
  2. custompurification by chromatography on silica gel

Sources & evidence

ORD record
ord-a1da06f9d7d643b6a8b57076fe50fe6c
Source dataset
uspto-grants-2003_04
Patent number
US06545037B2

Reaction notes

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