Cesium carbonate → HCID 53628388, compound

HRID 1959031Notes

Reaction equation

HRID 1959031 reaction equation
N1([S:5]([NH2:8])(=[O:7])=[O:6])CCC1.C1(P([CH:37]2[CH2:42]CCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].[Si:49]([O:56][CH2:57][C@@H:58]([CH2:77][O:78][CH:79]([CH3:81])[CH3:80])[O:59][C:60]1[CH:65]=[C:64](Cl)[N:63]=[C:62]([S:67][CH2:68][C:69]2[CH:74]=[CH:73][CH:72]=[C:71]([F:75])[C:70]=2[F:76])[N:61]=1)([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Si:49]([O:56][CH2:57][C@@H:58]([CH2:77][O:78][CH:79]([CH3:81])[CH3:80])[O:59][C:60]1[N:61]=[C:62]([S:67][CH2:68][C:69]2[CH:74]=[CH:73][CH:72]=[C:71]([F:75])[C:70]=2[F:76])[N:63]=[C:64]([NH:8][S:5]([C:42]2[N:63]=[CH:62][N:61]([CH3:60])[CH:37]=2)(=[O:6])=[O:7])[CH:65]=1)([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 450805661-AzetidinesulfonamideHCID 53628391HCID 53628391, compound2×

Product 1

HCID 53628388HCID 53628388, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

The subtitle compound was prepared according to the procedure outlined in example 1 step (iv) using a mixture of azetidine-1-sulfonamide (prepared according to patent WO 2004/011443) (0.19 g), tris(dibenzylideneacetone)dipalladium (0) (0.53 g), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (39 mg), cesium carbonate (0.28 g), 4-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(isopropoxymethyl)ethoxy]-6-chloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of step iv) (0.3 g) and dioxane (15 mL). Purification was by column chromatography on silica gel using EtOAc/iso-hexane (2:8) 50:70 as eluent, to give the title compound as a white solid. Yield: 90 mg

Workup

  1. customThe subtitle compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-f3a2ae6c7c3849b4b0c1aacddde50666
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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