Sodium Carbonate → HCID 178481511, compound

HRID 1042079Notes

Reaction equation

HRID 1042079 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].C([O-])([O-])=O.[Na+].[Na+].Br[C:44]1[CH:45]=[C:46]([C@:50]2([CH3:66])[CH2:55][C:54](=[O:56])[N:53]([CH3:57])[C:52](=[N:58][C:59](=[O:65])[O:60][C:61]([CH3:64])([CH3:63])[CH3:62])[NH:51]2)[CH:47]=[CH:48][CH:49]=1>CN(C=O)C.CCOC(C)=O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].O>[F:9][S:8]([F:13])([F:12])([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:44]2[CH:49]=[CH:48][CH:47]=[C:46]([C@:50]3([CH3:66])[CH2:55][C:54](=[O:56])[N:53]([CH3:57])[C:52](=[N:58][C:59](=[O:65])[O:60][C:61]([CH3:63])([CH3:62])[CH3:64])[NH:51]3)[CH:45]=2)=[CH:3][CH:4]=1

Participants

10

Reactant 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 27791941-Bromo-4-(pentafluoro-lambda6-sulfanyl)benzeneHCID 178481508HCID 178481508, compound

Product 1

HCID 178481511HCID 178481511, compound

Reagents, catalysts & solvents 4

HCID 53485975CID 53485975Catalyst2×HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Stir 1-bromo-4-pentafluorosulfanylbenzene (100 mg) together with bis(pinacolato)diboron (90 mg), potassium acetate (104 mg) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (43 mg) in DMF (2 ml) at 80° C. for 2 h. Allow the reaction mixture to cool, then add Na2CO3 (225 mg), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (43 mg), water (0.7 ml) and (S)-tert-butyl 4-(3-bromophenyl)-1,4-dimethyl-6-oxo-tetrahydropyrimidin-2(1H)-ylidenecarbamate (240 mg). Stir the mixture at 80° C. for 3 h. Allow the reaction mixture to cool, dilute with EtOAc (20 ml) and wash with water (2×5 ml). Dry the organic layer (MgSO4), filter and evaporate the filtrate. Chromatograph the residue on a silica gel column and elute with EtOAc/hexanes to afford the product, (S)-tert-butyl 4-(4′-pentafluorosulfanylbiphenyl-3-yl)-1,4-dimethyl-6-oxotetrahydropyrimidin-2(1H)-ylidenecarbamate.

Workup

  1. temperatureto cool
  2. temperatureto cool
  3. washwash with water (2×5 ml)
  4. dry with materialDry the organic layer (MgSO4)
  5. filtrationfilter
  6. customevaporate the filtrate
  7. washChromatograph the residue on a silica gel column and elute with EtOAc/hexanes

Sources & evidence

ORD record
ord-0af9f622668649b5b3ac04d7d4531921
Source dataset
uspto-grants-2013_10
Patent number
US08557826B2

Reaction notes

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