Cesium carbonate → HCID 42613224, compound

HRID 74696Notes

Reaction equation

C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[CH3:47][O:48][C:49]1[CH:50]=[CH:51][C:52]2[NH:58][C:57](=[O:59])[N:56]([CH:60]3[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]3)[CH2:55][CH2:54][C:53]=2[CH:66]=1.Br[C:68]1[CH:69]=[C:70]([C:74]([N:76]2[C:84]3[C:79](=[CH:80][C:81]([F:85])=[CH:82][CH:83]=3)[CH2:78][CH2:77]2)=[O:75])[CH:71]=[CH:72][CH:73]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:85][C:81]1[CH:80]=[C:79]2[C:84](=[CH:83][CH:82]=1)[N:76]([C:74]([C:70]1[CH:69]=[C:68]([N:63]3[CH2:64][CH2:65][CH:60]([N:56]4[CH2:55][CH2:54][C:53]5[CH:66]=[C:49]([O:48][CH3:47])[CH:50]=[CH:51][C:52]=5[NH:58][C:57]4=[O:59])[CH2:61][CH2:62]3)[CH:73]=[CH:72][CH:71]=1)=[O:75])[CH2:77][CH2:78]2

Participants

Conditions

Temperature: 120 °C

Procedure

Under an argon atmosphere 7 mg (31 μmol) palladium(II) acetate and 20 mg (32 μmol) BINAP were added to 86 mg (0.31 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 0.10 g (0.31 mmol) (3-bromo-phenyl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone and 0.16 g (0.48 mmol) caesium carbonate in 4.0 mL dioxane, and the mixture was stirred overnight at 120° C. The reaction mixture was then evaporated down and the residue was dissolved in DMF/MeOH and purified by preparative HPLC-MS.

Workup

customThe reaction mixture was then evaporated down
dissolutionthe residue was dissolved in DMF/MeOH
custompurified by preparative HPLC-MS

Sources & evidence

ORD record: ord-e362fb5fa5d146cbad74cb0a1be41ce0
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829006B2

Reaction notes

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