Cesium carbonate → HCID 57635810, compound

HRID 2109922Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=1[O:14][CH3:15])(=O)=O.[C:18](=[N:31][NH2:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.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(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:15][O:14][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([CH3:13])[C:7]=1[NH:32][N:31]=[C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-methoxy-6-methylphenyl trifluoromethanesulfonate (3.0 g, 0.011 mol), benzophenone hydrazone (2.38 g, 0.012 mol), BINAP (0.691 g, 0.001 mol), and cesium carbonate (5.06 g, 0.016 mol) in toluene (50 mL) was degassed with nitrogen. Palladium (II) acetate (0.075 g, 0.33 mol) was added, and the mixture was heated to 100° C. for 16 h. Reaction completion was judged by TLC (Eluent—5% EtOAc/Hexanes). The mixture was cooled to rt, concentrated under vacuum, and purified by silica gel chromatography using a gradient of hexanes—10% EtOAc/hexanes to afford 3.40 g (97%) of diphenylmethanone (2-methoxy-6-methylphenyl)hydrazone. 1H NMR (400 MHz, CD2Cl2) δ 7.65 (m, 2H), 7.55 (m, 3H), 7.40 (m, 2H), 7.30 (m, 3H), 6.85 (m, 2H), 6.68 (m, 1H), 3.70 (s, 3H), 2.67 (s, 3H); ES-MS m/z 317.1 (MH+); HPLC RT (min) 4.23.

Workup

customwas degassed with nitrogen
customReaction completion
temperatureThe mixture was cooled to rt
concentrationconcentrated under vacuum
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-e212841ddeb14c10a71f434e7aaed3f2
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517878B2

Reaction notes

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