Triphenylphosphine → 3-(6-Methoxy-4-thiazol-2-yl-phthalazin-1-yl)-propionic acid ethyl ester

HRID 2297490Notes

Reaction equation

HRID 2297490 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10](Cl)=[N:9][N:8]=1)[CH3:2].Br[C:22]1[S:23][CH:24]=[CH:25][N:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Zn].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[N:9][N:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 764302-BromothiazoleHCID 867576483-(4-Chloro-6-methoxy-phthalazin-1-yl)-propionic acid ethyl ester

Product 1

HCID 540412213-(6-Methoxy-4-thiazol-2-yl-phthalazin-1-yl)-propionic acid ethyl esterYield 26.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 167845palladium(II) acetateCatalyst

Procedure

Operating analogously at what described in example 48 starting from 3-(4-chloro-6-methoxy-phthalazin-1-yl)-propionic acid ethyl ester (4.5 g, 0.0153 mole), prepared as described in example 121, zinc (2.2 g), 2-bromothiazole (5 g, 0.0305 mole), palladium acetate (180 mg, 0.8 mmole), triphenyphosphine (630 mg, 2.4 mmoles), 1.4 g of the title compound were obtained (yield: 21%). m.p.: 153-154° C.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-046a365cb06e48bcad789c2ddf569e29
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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