Dichloromethane → HCID 131734329, compound

HRID 1504518Notes

Reaction equation

C[C:2]1([CH3:42])[C:28]2[C:23](=[C:24](P(C3C=CC=CC=3)C3C=CC=CC=3)[CH:25]=[CH:26][CH:27]=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=C[C:3]1=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[NH2:51][C:52]1[CH:57]=[CH:56][C:55]([S:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[CH:54][C:53]=1/[CH:66]=[CH:67]/[C:68]([O:70][CH2:71][CH3:72])=[O:69].C(Cl)[Cl:74]>O1CCOCC1.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]>[CH2:59]([S:58][C:55]1[CH:56]=[CH:57][C:52]([NH:51][C:27]2[CH:26]=[CH:25][C:24]([Cl:74])=[CH:23][C:28]=2[CH:2]2[CH2:3][CH2:42]2)=[C:53](/[CH:66]=[CH:67]/[C:68]([O:70][CH2:71][CH3:72])=[O:69])[CH:54]=1)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The crude residue from the previous step was dissolved in 18 mL dioxane and was treated with xantphos (0.945 g, 1.633 mmol), pd2(dba)3 (0.374 g, 0.408 mmol), potassium phosphate (13.86 g, 65.3 mmol), and (E)-ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate (5.12 g, 16.33 mmol) and was heated to 100° C. overnight. The reaction mixture was then diluted with DCM and was washed with saturated NH4Cl solution. The organics were dried over MgSO4 and concentrated. The crude residue was used in the following step without purification. m/z (ESI) 464.2 (M+H)+.

Workup

washwas washed with saturated NH4Cl solution
dry with materialThe organics were dried over MgSO4
concentrationconcentrated
customThe crude residue was used in the following step without purification

Sources & evidence

ORD record: ord-162e16b47ab34bdeadd66d6d45ad29b4
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212182B2

Reaction notes

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