4-(Tri-n-butylstannyl)pyridine → 2,3-Dichloro-N-[5-(4-pyridinyl)-3-(3-pyridinylmethoxy)-2-pyrazinyl]benzenesulphonamide

HRID 1444041Notes

Reaction equation

HRID 1444041 reaction equation
Br[C:2]1[N:3]=[C:4]([O:27][CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[C:5]([N:8]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=2[Cl:26])(=[O:18])=[O:17])C(=O)OCC(C)C)=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:40]1[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=1)CCC.C(OCC)(=O)C.C(O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:26][C:20]1[C:21]([Cl:25])=[CH:22][CH:23]=[CH:24][C:19]=1[S:16]([NH:8][C:5]1[C:4]([O:27][CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)=[N:3][C:2]([C:40]2[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=2)=[CH:7][N:6]=1)(=[O:18])=[O:17]

Participants

6

Reactant 3

HCID 27373184-(Tri-n-butylstannyl)pyridineHCID 21584252Ethanol ethylacetateHCID 58597367[5-Bromo-3-(3-pyridinylmethoxy)-2-pyrazinyl][(2,3-dichlorophenyl)sulphonyl]carbamic acid, 2-methylpropyl ester

Product 1

HCID 591682082,3-Dichloro-N-[5-(4-pyridinyl)-3-(3-pyridinylmethoxy)-2-pyrazinyl]benzenesulphonamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

[5-Bromo-3-(3-pyridinylmethoxy)-2-pyrazinyl][(2,3-dichlorophenyl)sulphonyl]carbamic acid, 2-methylpropyl ester (Example 136a) (0.11 g), 4-tributylstannanylpyridine (0.067 g) and tetrakis(triphenylphosphine)palladium(0) (0.05 g) in toluene (3 mL) was heated at 95° C. for 16 h. Chromatography on silica gel eluting with ethyl acetate/ethanol mixtures gave the title compound protected with the 2-methylpropylcarbonyl group (0.09 g). The compound was heated at 60° C. in methanol (2 mL) and 1M sodium hydroxide (0.36 mL) for 1 h. The solution was evaporated. Purification was by reverse phase preparative high pressure liquid chromatography. Yield 0.015 g.

Sources & evidence

ORD record
ord-dbcb24c885b94ceb84f6fc9fc95fa183
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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