Cesium carbonate → HCID 66835009, compound

HRID 2275299Notes

Reaction equation

[CH3:1][C:2]1([CH3:28])[C:14]2[O:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10]=2C(=O)[C:8]2[C:3]1=[CH:4][C:5](OS(C(F)(F)F)(=O)=O)=[CH:6][CH:7]=2.C(=[NH:42])(C1C=CC=CC=1)C1C=CC=CC=1.[C:43](=[O:46])([O-])[O-].[Cs+].[Cs+].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>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1COCC1>[NH2:42][C:5]1[CH:4]=[C:3]2[C:8](=[CH:7][CH:6]=1)[C:43](=[O:46])[C:10]1[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[O:13][C:14]=1[C:2]2([CH3:28])[CH3:1]

Participants

Conditions

Temperature: 65 °C

Procedure

To trifluoro-methanesulfonic acid 6,6-dimethyl-11-oxo-6,11-dihydro-benzo[b]naphtho[2,3-d]furan-8-yl ester (100 mg), benzhydrylideneamine (0.05 ml), cesium carbonate (110 mg), palladium acetate (2 mg) and BINAP (7 mg), THF (2 ml) was added. The mixture was stirred and heated at 65° C. overnight under nitrogen atmosphere, and the reaction mixture was diluted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (16 mg, 23%).

Workup

washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
concentrationconcentrated under reduced pressure
customThe resulting residues were purified by silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-9e3d5d25c11a43d280d10d7610de2af3
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126931B2

Reaction notes

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