Triphenylphosphine → HCID 10173143, compound

HRID 1582160Notes

Reaction equation

HRID 1582160 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][N:27]=1)[C:5]([NH:7][C:8]1[S:9][C:10]2[C:16]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:15][CH:14]=[C:13]([O:23][CH3:24])[C:11]=2[N:12]=1)=[O:6].[CH:28]([Sn](CCCC)(CCCC)CCCC)=[CH:29][C:30](=C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Li+].C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C>CN(C=O)C.[Pd].ClCCl.CO.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>[CH:29]([C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][N:27]=1)[C:5]([NH:7][C:8]1[S:9][C:10]2[C:16]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:15][CH:14]=[C:13]([O:23][CH3:24])[C:11]=2[N:12]=1)=[O:6])([CH3:30])[CH3:28]

Participants

11

Reactant 5

HCID 11776TriphenylphosphineHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 433294Lithium ChlorideHCID 227195382-Bromo-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-isonicotinamideHCID 71341101Tributyl(3-methylbuta-1,3-dien-1-yl)stannane

Product 1

HCID 10173143HCID 10173143, compound

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

From 2-bromo-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-isonicotinamide with isoprenyltri-n-butyltin, bis(triphenylphosphine)palladium(II) chloride, triphenylphosphine, lithium chloride and 2,6-di-tert-butyl-para-cresol in DMF, then hydrogenation with palladium on charcoal in dichloromethane and methanol. ES-MS m/e (%): 412 (M+H+, 100).

Sources & evidence

ORD record
ord-e519e93cf0de45048951008c27dc6b29
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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