Cesium carbonate → HCID 67431344, compound

HRID 2036675Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Br[C:50]1[CH:51]=[C:52]([N:56]2[C:60]3[CH:61]=[C:62]([F:65])[CH:63]=[CH:64][C:59]=3[N:58]=[C:57]2[CH:66]([NH:68][C:69](=[O:71])[CH3:70])[CH3:67])[CH:53]=[N:54][CH:55]=1.[CH3:72][S:73]([NH2:76])(=[O:75])=[O: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]>[F:65][C:62]1[CH:63]=[CH:64][C:59]2[N:58]=[C:57]([CH:66]([NH:68][C:69](=[O:71])[CH3:70])[CH3:67])[N:56]([C:52]3[CH:53]=[N:54][CH:55]=[C:50]([NH:76][S:73]([CH3:72])(=[O:75])=[O:74])[CH:51]=3)[C:60]=2[CH:61]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a microwave vial was added cesium carbonate (1.30 g, 3.98 mmol), Pd2(dba)3 (0.146 g, 0.159 mmol), Xantphos (0.230 g, 0.398 mmol), N-(1-(1-(5-bromopyridin-3-yl)-6-fluoro-1H-benzo[d]imidazol-2-yl)ethyl)acetamide (0.600 g, 1.59 mmol), and methanesulfonamide (0.166 g, 1.75 mmol) in dioxane (7.95 mL). The suspension was purged with nitrogen for 5 min then was stirred at 120° C. for 3 h under microwave irradiation. The solution was loaded directly onto silica gel then purified by MPLC (eluted with a gradient of 0-10% MeOH in DCM) to afford N-(1-(6-fluoro-1-(5-(methylsulfonamido)pyridin-3-yl)-1H-benzo[d]imidazol-2-yl)ethyl)acetamide as an off-white solid. LC-MS (ESI) m/z 392.1 [M+H]+.

Workup

customThe suspension was purged with nitrogen for 5 min
customthen purified by MPLC (
washeluted with a gradient of 0-10% MeOH in DCM)

Sources & evidence

ORD record: ord-e7a0ecf519c44fa799c222fef191cd43
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575183B2

Reaction notes

Loading…