Sodium Carbonate → HCID 53443277, compound

HRID 1755141Notes

Reaction equation

I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[O:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[C:10]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O>[O:9]1[C:10]2=[CH:11][CH:12]=[CH:17][C:16]2=[CH:15][CH:14]=[C:13]1[NH:6][C:5]1[CH:7]=[CH:8][CH:2]=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 4-iodo-aniline (25.0 g, 114.1 mmol), 2-benzofuran-boronic acid (27.7 g, 171.2 mmol), PdCl2(O-tolylphosphine) (11.66 g, 14.8 mmol), and Na2CO3(60.49 g, 570.7 mmol) in DME/EtOH/H2O (4:2:1)(700 mL) was heated at 125° C. for 2 h. The reaction mixture was cooled to room temperature, filtered and washed. The solvent was removed under reduced pressure. The residue was partitioned (ethyl acetate/water) and the organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting crude was purified by column chromatography on silica gel, eluting with dichloromethane to afford 4-benzofuran-2-yl-phenylamine (11) as a pale yellow solid (23.78 g, 99.5%): 1H NMR (300 MHz, CDCl3): δ 7.66 (d, J=9.0 Hz, 2H), 7.51-7.55 (m, 2H), 7.20-7.23 (m, 2H), 6.81 (s, 1H), 6.73 (d, J=9.0 Hz, 2H), 3.83 (bs, 2H) TLC conditions: Uniplate silica gel, 250 microns; mobile phase=ethyl acetate/hexanes (2:1); Rf=0.45.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
washwashed
customThe solvent was removed under reduced pressure
customThe residue was partitioned (ethyl acetate/water)
washthe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe resulting crude was purified by column chromatography on silica gel
washeluting with dichloromethane

Sources & evidence

ORD record: ord-4410fa6ceaf84c25a1f884d6c4a241c4
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169201B2

Reaction notes

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