Hydrochloric Acid → HCID 59128275, compound

HRID 1990840Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:10]2[O:14]CCO2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH2:15]([NH2:17])[CH3:16].CC(C)([O-])C.[Na+].Cl>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:15]([NH:17][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH3:9])[CH:10]=[O:14])[CH3:16]

Participants

Conditions

Temperature: 110 °C

Procedure

Through a solution of 2-(3-bromo-4-methoxy-phenyl)-[1,3]dioxolane (1.2 g, 4.63 mmol, 1.0 equiv; prepared as described in WO 01/74775 A1, Sanofi-Synthelabo) in toluene (6 mL) was bubbled ethylamine for 10 min. To this solution was added sodium tert-butoxide (0.67 g, 6.95 mmol, 1.5 equiv), (±)-BINAP (0.029 g, 0.046 mmol, 0.01 equiv) and Pd2(dba)3 (Tris(dibenzylideneacetone)dipailadium, 0.021 g, 0.023 mmol, 0.005 equiv) and the solution heated to 110° C. under microwave irradiation for 20 min. A few drops of a solution of 37% HCl were added and the reaction mixture heated again to 100° C. under microwave irradiation for 5 min. Evaporation of the solvent and purification of the crude reaction product by column chromatography on silica eluting with hexane/ethyl acetate (7:3) provided 0.52 g (63%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.24 (t, J=7.1 Hz, 3H), 3.16 (q, J=7.1 Hz, 2H), 3.86 (s, 3H), 4.17 (br s, 1H), 6.78 (d, J=8.1 Hz, 1H), 7.01 (d, J=1.9 Hz, 1H), 7.13 (dd, J=8.1 Hz, J=1.9 Hz, 1H). MS (ISP): 179.9 [M+H]+.

Workup

temperaturethe reaction mixture heated again to 100° C. under microwave irradiation for 5 min
customEvaporation of the solvent and purification of the crude
customreaction product by column chromatography on silica eluting with hexane/ethyl acetate (7:3)

Sources & evidence

ORD record: ord-60274e576b92442a8a6944cfd75672c2
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645753B2

Reaction notes

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