Methylamine → Ethyl 4-fluoro-2-hydroxy-5-[2-[4-[(3-methyl-2-pyridinylamino)-sulfonyl]phenyl]ethenyl]benzoate

HRID 743028Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)=[CH2:2].[F:20][C:21]1[C:31](I)=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:23]([OH:33])[CH:22]=1.CN.CN(C)C(=O)C>C(Cl)(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[F:20][C:21]1[C:31]([CH:2]=[CH:1][C:3]2[CH:4]=[CH:5][C:6]([S:9]([NH:12][C:13]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]=3)(=[O:10])=[O:11])=[CH:7][CH:8]=2)=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:23]([OH:33])[CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

4-Ethenyl-N-(3-methyl-2-pyridinyl)benzenesulfonamide (2.7 g, 10 mmol), ethyl 4-fluoro-2-hydroxy-5-iodobenzoate (3.6 g, 80%, 10 mmol), methylamine (5 ml) and N,N-dimethylacetamide (5 ml) were mixed and heated to 50° C. Palladium acetate (40 mg) was added and the solution kept at 50° C. for 18 h. The solution was poured into water and the precipitate dissolved in chloroform. The solution was dried, applied on top of a short silica gel column and eluted with 30% isobutylmethylketone in toluene. The pure fractions were collected and evaporated to dryness. After trituration with acetonitril the product crystallized. Yield 1.1 g.

Workup

customThe solution was dried
washeluted with 30% isobutylmethylketone in toluene
customThe pure fractions were collected
customevaporated to dryness
customAfter trituration with acetonitril the product crystallized

Sources & evidence

ORD record: ord-973cd01c82374f429de365a3b4095811
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556855

Reaction notes

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