Cesium carbonate → HCID 86706575, compound

HRID 1048856Notes

Reaction equation

[C:1]1([C@H:11]([NH:13][C:14]([CH:16]2[O:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[O:15])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25](I)[CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:22][C:23]1[CH:24]=[C:25]([N:18]2[CH2:19][CH2:20][O:21][CH:16]([C:14]([NH:13][C@@H:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[CH3:12])=[O:15])[CH2:17]2)[CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture solution of N-((R)-1-(naphthalen-1-yl)ethyl)morpholine-2-carboxamide (Intermediate-2) (300 mg, 1.056 mmol) in toluene (10 mL), bis(tri-tert butyl phosphine) Pd(0) (0.10, 54 mg), trisdibenzylidene acetone dipalladium(0) (48 mg, 0.0528 mmol), 1-fluoro-3-iodobenzene (0.15 ml, 1.26 mmol) and Cs2CO3 (516 mg, 1.58 mmol) were added. The reaction mass was heated to 110° C. and further maintained for 15 h under nitrogen atmosphere. The mixture was diluted with ethyl acetate, filtered through celite bed, and concentrated under vacuum. It was further purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane as eluent to afford title compound as oily mass (250 mg), m/z: 379.2.

Workup

temperaturefurther maintained for 15 h under nitrogen atmosphere
filtrationfiltered through celite bed
concentrationconcentrated under vacuum
customIt was further purified by column chromatography on silica gel using
additiona mixture of ethyl acetate and hexane as eluent

Sources & evidence

ORD record: ord-83dcdf23164240ac9e1f35edc97beb9e
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382216B2

Reaction notes

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