Triphenylphosphine → HCID 10151608, compound

HRID 1167760Notes

Reaction equation

HRID 1167760 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]([N: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].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Li+].C(C1[CH:58]=[C:57](C)[CH:56]=[C:55](C(C)(C)C)[C:54]=1[OH:64])(C)(C)C>CN(C=O)C.[Pd].CO.ClCCl.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>[CH3:24][O:23][C:13]1[C:11]2[N:12]=[C:8]([NH:7][C:5](=[O:6])[C:4]3[CH:25]=[CH:26][N:27]=[C:2]([CH:56]4[CH2:57][CH2:58][O:64][CH2:54][CH2:55]4)[CH:3]=3)[S:9][C:10]=2[C:16]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:15][CH:14]=1

Participants

10

Reactant 4

HCID 11776TriphenylphosphineHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 433294Lithium ChlorideHCID 229934292-bromo-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide

Product 1

HCID 10151608HCID 10151608, compound

Reagents, catalysts & solvents 5

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

Procedure

From 2-bromo-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide with tri-n-butyl-(3,6-dihydro-2H-pyrin-4-yl)-stannane, bis(triphenylphosphine)palladium(II) chloride, triphenylphosphine, lithium chloride and 2,6-di-tert-butyl-4-methylphenol in DMF. Then hydrogenation using palladium on charcoal in methanol and dichloromethane. ES-MS m/e (%): 477 (M+Na+, 16), 455 (M+H+, 100).

Sources & evidence

ORD record
ord-9df9d99e56a14e95a8022f969214d57b
Source dataset
uspto-grants-2003_09
Patent number
US06620811B2

Reaction notes

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