Tributylamine → Isobutyl 2-hydroxy-5-[2-[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoate

HRID 1653906Notes

Reaction equation

HRID 1653906 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12](I)=[CH:11][C:3]=1[C:4]([O:6][CH2:7][CH:8]([CH3:10])[CH3:9])=[O:5].[CH:16]([C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][N:29]=2)(=[O:26])=[O:25])=[CH:20][CH:19]=1)=[CH2:17].C(N(CCCC)CCCC)CCC>CC(N(C)C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:1][C:2]1[CH:14]=[CH:13][C:12]([CH:17]=[CH:16][C:18]2[CH:19]=[CH:20][C:21]([S:24]([NH:27][C:28]3[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][N:29]=3)(=[O:25])=[O:26])=[CH:22][CH:23]=2)=[CH:11][C:3]=1[C:4]([O:6][CH2:7][CH:8]([CH3:10])[CH3:9])=[O:5]

Participants

6

Reactant 3

HCID 7622TributylamineHCID 194233654-Ethenyl-N-(3-methyl-2-pyridinyl)benzenesulfonamideHCID 19423370Isobutyl 2-hydroxy-5-iodobenzoate

Product 1

HCID 54356729Isobutyl 2-hydroxy-5-[2-[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Procedure

Isobutyl 2-hydroxy-5-iodobenzoate (70.2 g, 0.22 mol) and 4-ethenyl-N-(3-methyl-2-pyridinyl)benzenesulfonamide (54.8 g, 0.20 mol) were suspended in a solution of tributylamine (55.5 g, 0.3 mol) and palladium(II) acetate (0.44 g 0.0022 mol) in dimethylacetamide (200 ml).

Sources & evidence

ORD record
ord-54b4c262068749baa726ce2e9d1fa146
Source dataset
uspto-grants-1995_04
Patent number
US05403930

Reaction notes

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