Divinyl sulfone → HCID 59156653, compound

HRID 2390885Notes

Reaction equation

HRID 2390885 reaction equation
C(S(C=C)(=O)=[O:4])=C.CC1(C)CC(C)OB(/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=2)O1.[CH3:30][C:31]([C:33]([C@@H:35]1N[C:39]2[C:41](N=C(N)N[C:38]=2[NH:37][CH2:36]1)=O)=O)=O.[C:47]([O-:50])([O-])=O.[Na+].[Na+].C(Cl)Cl.[CH3:56][OH:57].[C:58]1([CH3:64])[CH:63]=[CH:62][CH:61]=C[CH:59]=1>[Pd]>[CH3:56][O:57][C:63]1([C:58]2[C:59]([O:50][CH3:47])=[C:30](/[CH:16]=[CH:17]/[C:18]3[CH:19]=[CH:20][C:21]([NH:24][S:25]([CH3:28])(=[O:26])=[O:27])=[CH:22][CH:23]=3)[CH:31]=[C:33]([C:35]3[C:36](=[O:4])[NH:37][CH:38]=[CH:39][CH:41]=3)[CH:64]=2)[CH2:62][CH2:61]1

Participants

7

Reactant 5

HCID 6496Divinyl sulfoneHCID 10340Sodium CarbonateHCID 19384728HCID 19384728, compoundHCID 59372471HCID 59372471, compoundHCID 178472530HCID 178472530, compound

Product 1

HCID 59156653HCID 59156653, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

step 2—A mixture of 380 (0.14 g, 0.39 mmol), 242 (0.19 g, 0.59 mmol), Pd(PPh4 (0.045 g, 0.039 mmol) and Na2CO3 (0.12 g, 1.2 mmol) in DCM-MeOH-toluene (1:2:1, 4 mL) was irradiated in a microwave reactor at 120° C. for 60 min. The reaction mixture was filtered and the filtrate concentrated. The crude product was purified by SiO2 chromatography (DCM/MeOH/NH4OH) followed by preparative HPLC to afford I-266 and I-267.

Workup

  1. customwas irradiated in a microwave reactor at 120° C. for 60 min
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated
  4. customThe crude product was purified by SiO2 chromatography (DCM/MeOH/NH4OH)
  5. customto afford I-266 and I-267

Sources & evidence

ORD record
ord-4f69f9c2f49447fa9c8aed6b7c41cee1
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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