Indium → HCID 86713127, compound

HRID 1399457Notes

Reaction equation

[In].[F:2][C:3]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[C:4]=1[C:5]([NH:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6]>CC(O)=O.CCOC(C)=O>[NH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:3]([F:2])[C:4]=1[C:5]([NH:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of indium powder (237 mg, 2.07 mmol) in AcOH (2 mL) was added 2-(2-fluoro-6-nitrobenzamido)acetic acid (50 mg, 0.21 mmol) at rt and stirred at 60° C. for 30 min. The reaction mixture was attained to rt and diluted with EtOAc (20 mL). The solution was stirred for 5 min and filtered through celite. The celite bed was washed with EtOAc (10 mL) and the combined organic layer was evaporated under reduced pressure. The residue was chromatographed over silica gel column using chloroform:methanol (70:30) as eluents to give the product as a pale brown color solid (32 mg, 73%), mp 188-192° C. 1H NMR (400 MHz, CDCl3+DMSO-d6): δ 7.80 (2H, br s), 7.04 (1H, dd, J=15.0, 7.8 Hz), 6.50 (1H, d, J=8.4 Hz), 6.27 (1H, t, J=9.4 Hz), 6.26 (1H, br s, exchangeable with D2O), 3.74 (2H, d, J=3.6 Hz); 13C NMR (100 MHz, CDCl3+DMSO-d6): δ 172.7, 164.3, 160.7 (d, J=242 Hz), 150.1 (d, J=6 Hz), 130.9 (d, J=12 Hz), 111.5, 106.4 (d, J=18 Hz), 101.2 (d, J=24 Hz), 43.0; LC-MS (negative ion mode): m/z 211 (M−H)−.

Workup

customwas attained to rt
stirringThe solution was stirred for 5 min
filtrationfiltered through celite
washThe celite bed was washed with EtOAc (10 mL)
customthe combined organic layer was evaporated under reduced pressure
customThe residue was chromatographed over silica gel column

Sources & evidence

ORD record: ord-96fb2ec669fd4b12811c69bea23396b3
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906344B2

Reaction notes

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