Potassium Phosphate, Tribasic → (Z)-ethyl 3-(5-(benzylthio)-2-((4-bromo-5-chloro-2-methoxyphenyl)amino)phenyl)but-2-enoate

HRID 1504414Notes

Reaction equation

HRID 1504414 reaction equation
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[Br:43][C:44]1[CH:49]=[C:48]([O:50][CH3:51])[C:47](I)=[CH:46][C:45]=1[Cl:53].[NH2:54][C:55]1[CH:60]=[CH:59][C:58]([S:61][CH2:62][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)=[CH:57][C:56]=1/[C:69](/[CH3:76])=[CH:70]\[C:71]([O:73][CH2:74][CH3:75])=[O:72].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:62]([S:61][C:58]1[CH:59]=[CH:60][C:55]([NH:54][C:47]2[CH:46]=[C:45]([Cl:53])[C:44]([Br:43])=[CH:49][C:48]=2[O:50][CH3:51])=[C:56](/[C:69](/[CH3:76])=[CH:70]\[C:71]([O:73][CH2:74][CH3:75])=[O:72])[CH:57]=1)[C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 509978521-Bromo-2-chloro-4-iodo-5-methoxybenzeneHCID 117746848(Z)-ethyl 3-(2-amino-5-(benzylthio)phenyl)but-2-enoate

Product 1

HCID 131734327(Z)-ethyl 3-(5-(benzylthio)-2-((4-bromo-5-chloro-2-methoxyphenyl)amino)phenyl)but-2-enoate

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of xantphos (0.265 g, 0.458 mmol), pd2(dba)3 (0.140 g, 0.153 mmol), 1-bromo-2-chloro-4-iodo-5-methoxybenzene (1.167 g, 3.36 mmol), (Z)-ethyl 3-(2-amino-5-(benzylthio)phenyl)but-2-enoate (1.000 g, 3.05 mmol), and potassium phosphate (1.945 g, 9.16 mmol) in 10 mL dioxane was heated to 100° C. for 2 hours. The reaction mixture was then poured into water and extracted with DCM. The organics were dried over MgSO4 and concentrated. The crude residue was used in the next step without purification. m/z (ESI) 546.0 (M+H)+.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude residue was used in the next step without purification

Sources & evidence

ORD record
ord-1abe4f2d7b4845dda7e105731f2411cd
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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