tert-Butyl 4-(tributylstannyl)-3,6-dihydropyridine-1(2H)-carboxylate → HCID 86588830, compound

HRID 1582112Notes

Reaction equation

HRID 1582112 reaction equation
[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[S:6][C:7]2[C:13](I)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH:29]=[C:28]([Sn](CCCC)(CCCC)CCCC)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:18]([O:22][C:23]([N:25]1[CH2:26][CH:27]=[C:28]([C:13]2[C:7]3[S:6][C:5]([NH:4][C:3]([O:2][CH3:1])=[O:17])=[N:9][C:8]=3[C:10]([O:15][CH3:16])=[CH:11][CH:12]=2)[CH2:29][CH2:30]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 2

HCID 12094207tert-Butyl 4-(tributylstannyl)-3,6-dihydropyridine-1(2H)-carboxylateHCID 60117385(7-Iodo-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

Product 1

HCID 86588830HCID 86588830, compoundYield 36.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2.2 g (0.006 Mol) (7-iodo-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester in 60 ml DMF were added 3.4 g (0.007 Mol) 4-tributylstannanyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester, 0.424 g (0.001 Mol) PdCl2(PPh3)2 and 0.12 g (0.001 Mol) CuI. The mixture was heated at 100° C. for 19 h and then concentrated in vacuo. Flash chromatography (ethyl acetate/hexane 1:1) afforded 0.91 g (36%) 4-(4-methoxy-2-methoxycarbonylamino-benzothiazol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as a light yellow foam. ES-MS m/e (%): 362 ([M+H]+, 100).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43f2420cf8d84840862893d406a74fca
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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